- Synthesis of new fluorinated imidazolium ionic liquids and their prospective function as the electrolytes for lithium-ion batteries
-
Two fluorine-containing ionic liquids, 1-(2,2,2-trifluoroethyl)-3- methylimidazolium tosylate and 1-(2,2,2-trifluoroethyl)-3-methylimidazolium bis(trifluoromethanesulfonyl)imide (TFSI anion), were obtained in good yields and high purity via a green pathway procedure free of solvent and hazardous catalyst. The incorporation of CF3 moieties in imidazolium structure decreases the ILs TFSI melting point. The preliminary electrochemical results are very promising, a wide electrochemical stability up to 5.7 V vs Li +/Li for the fluorinated imidazolium with TFSI anion.
- Tran, Anh Ngoc,Van Do, Thanh-Nhan,Le, Loan-Phung My,Le, Thach Ngoc
-
-
Read Online
- Exploring Electrochemical C(sp3)-H Oxidation for the Late-Stage Methylation of Complex Molecules
-
The magic methyl effect, a dramatic boost in the potency of biologically active compounds from the incorporation of a single methyl group, provides a simple yet powerful strategy employed by medicinal chemists in the drug discovery process. Despite significant advances, methodologies that enable the selective C(sp3)-H methylation of structurally complex medicinal agents remain very limited. In this work, we disclose a modular, efficient, and selective strategy for the α-methylation of protected amines (i.e., amides, carbamates, and sulfonamides) by means of electrochemical oxidation. Mechanistic analysis guided our development of an improved electrochemical protocol on the basis of the classic Shono oxidation reaction, which features broad reaction scope, high functional group compatibility, and operational simplicity. Importantly, this reaction system is amenable to the late-stage functionalization of complex targets containing basic nitrogen groups that are prevalent in medicinally active agents. When combined with organozinc-mediated C-C bond formation, our protocol enabled the direct methylation of a myriad of amine derivatives including those that have previously been explored for the magic methyl effect. This synthesis strategy thus circumvents multistep de novo synthesis that is currently necessary to access such compounds and has the potential to accelerate drug discovery efforts.
- Ho, Justin S. K.,Lin, Song,Liu, Kaida,Mao, Kaining,Neurock, Matthew,Novaes, Luiz F. T.,Tanwar, Mayank,Terrett, Jack A.,Villemure, Elisia
-
supporting information
p. 1187 - 1197
(2022/02/05)
-
- KIF18A INHIBITORS
-
Compounds of formula (I): as defined herein, and synthetic intermediates thereof, which are capable of modulating KIF18A protein thereby influencing the process of cell cycle and cell proliferation to treat cancer and cancer-related diseases. The invention also includes pharmaceutical compositions, including the compounds, and methods of treating disease states related to the activity of KIF18A.
- -
-
Paragraph 0189; 0265-0266
(2021/02/12)
-
- PYRIDINE DERIVATIVES AS KIF18A INHIBITORS
-
Amide compounds of formula (I): as defined herein, and synthetic intermediates thereof, which are capable of modulating KIF18A protein thereby influencing the process of cell cycle and cell proliferation to treat cancer and cancer-related diseases. The invention also includes pharmaceutical compositions, including the compounds, and methods of treating disease states related to the activity of KIF18A.
- -
-
Paragraph 0298-0299
(2021/02/12)
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- Palladium-Catalyzed Fluoroarylation of gem-Difluoroenynes to Access Trisubstituted Trifluoromethyl Allenes
-
Various new transformations of gem-difluoroalkenes leading to trifluoromethyl substituted compounds have been well established in the past years. However, the development of new transformations of gem-difluoroenynes lags much behind. Herein is reported the fluoroarylation of 1,1-difluoro-1,3-enynes with aryl halides in the presence of silver fluoride affording trisubstituted trifluoromethyl allenes under the catalysis of palladium. The reaction features mild conditions, high functional-group tolerance, and high regioselectivity.
- Qi, Shutao,Gao, Shiquan,Xie, Xiaoxiao,Yang, Junfeng,Zhang, Junliang
-
supporting information
p. 5229 - 5234
(2020/07/15)
-
- METHOD FOR PRODUCING MERCAPTOPHENOL COMPOUND AND INTERMEDIATE OF SAID COMPOUND
-
A production method in which a mercaptophenol compound is obtained using an industrially preferred sulfur atom introduction reaction, and intermediate compounds of the mercaptophenol compound are provided. A method for producing a mercaptophenol compound in which a phenyl carbamate compound is produced using a phenol compound as a raw material, and then a sulfur atom is regioselectively introduced by a reaction with sulfur monochloride, and a phenyl mercaptocarbamate compound is produced as an intermediate.
- -
-
Paragraph 0328-0331
(2020/09/15)
-
- QUINAZOLINE DERIVATIVE AND USE THEREOF
-
The present invention relates to a series of quinazoline compounds, especially compounds as represented by formula (I), isomers thereof or pharmaceutically acceptable salts thereof, pharmaceutical compositions thereof, and use thereof as Pan-HER tyrosine kinase inhibitors.
- -
-
Paragraph 0230; 0231; 0233
(2020/11/26)
-
- Method for preparing hydrofluoroether through two-step process
-
The invention discloses a method for preparing hydrofluoroether through a two-step process. With the method provided by the invention, p-toluensulfonyl chloride and fluorine-containing alcohol are subjected to a reaction to obtain p-toluenesulfonate, and the p-toluenesulfonate and sodium alkoxide are subjected to a Williamson ether synthetic reaction to obtain the hydrofluoroether. The method disclosed by the invention has the advantages of cheap and low-toxicity raw materials, mild and controllable reaction conditions, and high yield.
- -
-
Paragraph 0055; 0056; 0067; 0068
(2019/07/10)
-
- Peptidylarginine deiminase inhibitor and application thereof
-
The invention belongs to the technical field of medicine, and particularly relates to a peptidylarginine deiminase PAD4 inhibitor compound shown in a formula (I) or pharmaceutically acceptable salts,stereoisomers and tautomers thereof, as well as pharmaceutical compositions, pharmaceutical preparations and application thereof. X, Y, R1, R2, R3, R4, R5, R7, R8, R9, ring B and m are as defined in the specification. The compound has inhibitory effect on peptidylarginine deiminase PAD4, and can be used for treating various diseases, such as rheumatoid arthritis, vasculitis, systemic lupus erythematosus, ulcerative colitis, multiple sclerosis, cystic fibrosis, cancer, cutaneous lupus erythematosus, asthma and psoriasis.
- -
-
Paragraph 0762; 0764; 0765; 0766
(2019/09/10)
-
- BICYCLIC COMPOUNDS AS INHIBITORS OF PD1/PD-L1 INTERACTION/ACTIVATION
-
The compounds of Formula I is described herein along with their polymorphs, stereoisomers, tautomers, prodrugs, solvates, and pharmaceutically acceptable salts thereof. The compounds described herein, their polymorphs, stereoisomers, tautomers, prodrugs, solvates, and pharmaceutically acceptable salts thereof are bicyclic compounds that are inhibitors of PD-1/PD-L1 interaction/activation.
- -
-
Paragraph 00098
(2019/10/04)
-
- Rhodium-Catalyzed Defluorinative Vinylation of gem-Difluoroalkenes for the Synthesis of 2-Fluoro-1,3-dienes
-
Herein, we present a strategy for the formation of 2-fluoro-1,3-diene derivatives via rhodium-catalyzed direct C(sp2)—C(sp2) cross-coupling of gem-difluoroalkenes and acrylamides. By merging Rh(III)-catalyzed C(sp2)–H bond activation and nucleophilic addition/F-elimination of gem-difluoroalkene, an efficient defluorinative vinylation reaction is uncovered, which leads to the generation of 2-fluoro-1,3-dienes in moderate to good yields with excellent stereoselectivity under mild conditions. Preliminary mechanistic study suggests unique effects of fluorine substituents which allow the reactivity profile not observed with the congeners bearing heavier halides.
- Song, Shengjin,Liu, Huan,Wang, Lu,Zhu, Chuan,Loh, Teck-Peng,Feng, Chao
-
supporting information
p. 1036 - 1040
(2019/09/16)
-
- Rhodium(III)-Catalyzed Oxidative Annulation of Ketoximes with Sulfonamide: A Direct Approach to Indazoles
-
A rhodium(III)-catalyzed intermolecular C-H amination of ketoxime and iodobenzene diacetate-enabled N-N bond formation in the synthesis of indazoles has been developed. A variety of functional groups were well tolerated, providing the corresponding products in moderate to good yields. Moreover, the nitro-substituted ketoximes are well compatible in this reaction, leading to the corresponding products in moderate to good yields.
- Wang, Ning,Liu, Lingling,Xu, Wentao,Zhang, Mengye,Huang, Zhibin,Shi, Daqing,Zhao, Yingsheng
-
supporting information
p. 365 - 368
(2019/01/24)
-
- Neighboring phenolic group-activated: Gem -difluoroallylboration of imines for the catalyst-free synthesis of gem -difluorohomoallylamines
-
We herein report an unprecedented addition reaction of pinacol gem-difluoroallylborates and imines enabled by a neighboring phenolic group in an N-protecting group under catalyst-free conditions, thus facilitating the construction of a wide range of racemic gem-difluorohomoallylamine derivatives. Based on the control experiments, a plausible transition state via the Zimmerman-Traxler model was proposed to elucidate the significance of the neighboring phenolic group, as well as the γ-selectivity of the boronate reagents.
- Yang, Xing,Zhang, Feng,Zhou, Yang,Huang, Yi-Yong
-
supporting information
p. 3367 - 3371
(2018/05/23)
-
- Synthesis and evaluation of antiplasmodial activity of 2,2,2-trifluoroethoxychalcones and 2-fluoroethoxy chalcones against plasmodium falciparum in culture
-
A new class of compounds comprising two series of chalcones with 2,2,2-trifluoroethoxy group and 2-fluoroethoxy groups were synthesized and screened for in vitro antiplasmodial activity against Plasmodium falciparum (3D7) using the [3H] hypoxanthine incorporation inhibition assay. Chalcones with 2,2,2-trifluoroethoxy groups substituted on the p- and m-positions of the 1-phenyl ring showed weak antiplasmodial activity, while compounds substituted on the o-position of the 1-phenyl ring displayed enhanced antiplasmodial activity, thus indicating that 2,2,2-trifluoroethoxy groups on the 1-phenyl ring of chalcones show position-dependent antiplasmodial activity. Of the 34 compounds synthesized, chalcones 3a and 3f exhibited significant inhibitory effects, with IC50 values of 3.0 μg/mL and 2.2 μg/mL, respectively. Moreover, these compounds 3a and 3f showed profound antiplasmodial activity in combination with artemisinin in vitro. The most active molecules, 3a, and 3f, were further assessed for their cytotoxicity towards mammalian Vero cells and the selectivity index (SI) values are 8.6, and 8.2 respectively, being considered non-toxic. We also studied the antiplasmodial activity of 2-fluoroethoxychalcones to discern the effect of the number of fluorine atoms in the fluoroethoxy group. Our results showed that chalcones with 2-fluoroethoxy group on the 1-phenyl ring exhibited more enhanced inhibitory effects on the growth of parasites than their trifluoro analogues, which reveals that monofluoroethoxy group is generally more effective than trifluoroethoxy group in the inhibition of parasite growth. Thus o-2,2,2-trifluoroethoxychalcones (Series 3) and 2-fluoroethoxychalcones may serve as good antiplasmodial candidates for future further development.
- Devi, Kavita,Rajendran, Vinoth,Ayushee,Rangarajan,Singh, Rishi Pal,Ghosh, Prahlad C.,Singh, Manjula
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-
- Methods for Making Functionalized Fluorinated Monomers, Fluorinated Monomers, and Compositions for Making the Same
-
A method of making a functionalized fluorinated monomer for use in making oligomers and polymers that can be used to improve surface properties of polymer-derived systems, such as coatings. The method of making a functionalized fluorinated monomer includes reacting at least one fluorinated nucleophilic reactant, such as a fluorinated alcohol, with at least one compound containing at least one epoxide group. Other methods include reaction of a fluorinated alcohol with a cyclic carboxylic anhydride. In another embodiment, a method includes reacting a fluorinated mesylate, tosylate or triflate with an amine, alkoxide or phenoxide. In other embodiments, the method includes reacting a fluorinated alcohol with an alkyl halide, or reacting a fluorinated alkyl halide with an amine. The functionalized fluorinated monomers may be used as intermediates and reacted to modify the functional groups thereon. Further, the functionalized fluorinated monomers may be reacted to form polymers or oligomers, or with polymers or oligomers having functional groups to modify the polymer or oligomer through the functional group thereon,
- -
-
Paragraph 0221
(2018/12/04)
-
- Synthesis and physical properties of new fluoroether sulfones
-
Eight new strategically designed fluoroether sulfone solvents have been synthesized through different synthetic pathways for potential applications in lithium-sulfur battery electrolytes. The structures of these compounds have been confirmed by 1H-NMR, 13C-NMR and elemental analysis. Several 1,2-dimethoxyethane (DME)-based electrolyte formulations have been prepared with these solvents to derive an electrolyte with good ionic conductivity (>5 mS cm?1 at 25 ℃). The viscosity of these new additives has also been determined as it is directly related to the ionic conductivity. Three of these solvents that contain a trifluoromethyl group displayed acceptable ionic conductivity.
- Yue, Zheng,Mei, Xinyi,Dunya, Hamza,Ma, Qiang,McGarry, Christopher,Mandal, Braja K.
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p. 118 - 123
(2018/11/10)
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- Rapid transformation of sulfinate salts into sulfonates promoted by a hypervalent iodine(III) reagent
-
An alternative method for forming sulfonates through hypervalent iodine(III) reagent-mediated oxidation of sodium sulfinates has been developed. This transformation involves trapping reactive sulfonium species using alcohols. With additional optimization of the reaction conditions, the method appears extendable to other nucleophiles such as electron-rich aromatic systems or cyclic ethers through a ring opening pathway.
- Deruer, Elsa,Hamel, Vincent,Blais, Samuel,Canesi, Sylvain
-
supporting information
p. 1203 - 1207
(2018/06/04)
-
- Experimental and Theoretical Studies on Rhodium-Catalyzed Coupling of Benzamides with 2,2-Difluorovinyl Tosylate: Diverse Synthesis of Fluorinated Heterocycles
-
Fluorinated heterocycles play an important role in pharmaceutical and agrochemical industries. Herein, we report on the synthesis of four types of fluorinated heterocycles via rhodium(III)-catalyzed C-H activation of arenes/alkenes and versatile coupling with 2,2-difluorovinyl tosylate. With N-OMe benzamide being a directing group (DG), the reaction delivered a monofluorinated alkene with the retention of the tosylate functionality. Subsequent one-pot acid treatment allowed the efficient synthesis of 4-fluoroisoquinolin-1(2H)-ones and 5-fluoropyridin-2(1H)-ones. When N-OPiv benzamides were used, however, [4 + 2] cyclization occurred to provide gem-difluorinated dihydroisoquinolin-1(2H)-ones. Synthetic applications have been demonstrated and the ready availability of both the arene and the coupling partner highlighted the synthetic potentials of these protocols. Mechanistically, these two processes share a common process involving N-H deprotonation, C-H activation, and olefin insertion to form a 7-membered rhodacycle. Thereafter, different reaction pathways featuring β-F elimination and C-N bond formation are followed on the basis of density functional theory (DFT) studies. These two pathways are DG-dependent and led to the open chain and cyclization products, respectively. The mechanistic rationale was supported by detailed DFT studies. In particular, the origins of the intriguing selectivity in the competing β-F elimination versus C-N bond formation were elucidated. It was found that β-F elimination is a facile event and proceeds via a syn-coplanar transition state with a low energy barrier. The C-N bond formation proceeds via a facile migratory insertion of the Rh-C(alkyl) into the Rh(V) amido species. In both reactions, the migratory insertion of the alkene is turnover-limiting, which stays in good agreement with the experimental studies.
- Wu, Jia-Qiang,Zhang, Shang-Shi,Gao, Hui,Qi, Zisong,Zhou, Chu-Jun,Ji, Wei-Wei,Liu, Yao,Chen, Yunyun,Li, Qingjiang,Li, Xingwei,Wang, Honggen
-
supporting information
p. 3537 - 3545
(2017/03/15)
-
- Heteroannulation enabled by a bimetallic Rh(III)/Ag(i) relay catalysis: Application in the total synthesis of aristolactam BII
-
A redox-neutral bimetallic Rh(iii)/Ag(i) relay catalysis allowed the efficient construction of 3-alkylidene isoindolinones and 3-alkylidene isobenzofuranones. The Rh(iii) catalyst was responsible for the C-H monofluoroalkenylation reaction, whereas the Ag(i) salt was an activator for the follow-up cyclization. The methodology developed was applied as a key step in the rapid total synthesis of the natural product aristolactam BII.
- Ji, Wei-Wei,Lin,Li, Qingjiang,Wang, Honggen
-
supporting information
p. 5665 - 5668
(2017/07/07)
-
- Nonconventional difluoroalkylation of C(sp2)-H bonds through hydroarylation
-
An unprecedented Rh-catalyzed C2-difluoroalkylation of indole derivatives with 2,2-difluorovinyl arenesulfonates has been reported. This reaction provides a rare instance of catalytic difluoroalkylation through hydroarylation of gem-difluoroalkenes. The sulfonate group works as a chelating ligand, thus stabilizing the rhodacycle intermediate, leading to the uncommon transformation.
- Zhu, Chuan,Song, Shengjin,Zhou, Lu,Wang, Ding-Xing,Feng, Chao,Loh, Teck-Peng
-
supporting information
p. 9482 - 9485
(2017/09/01)
-
- Pd-catalyzed gem-difluoroallylation of arylboronic acids with γ,γ-difluoroallylic acetates
-
A highly regio- and stereo-selective palladium-catalyzed gem-difluoroallylation of arylboronic acids with γ,γ-difluoroallylic acetates has been described. The method allows the synthesis of a variety of gem-difluoroallylated arenes with a tosyloxy group on the CC double bond, thus providing a good opportunity for down-stream transformations.
- Zhang, Bo,Zhang, Xingang
-
supporting information
p. 1238 - 1241
(2016/01/15)
-
- LIQUID CRYSTAL COMPOUND, LIQUID CRYSTAL COMPOSITION, AND LIQUID CRYSTAL DISPLAY DEVICE
-
PROBLEM TO BE SOLVED: To provide a liquid crystal compound, a liquid crystal composition, and a liquid crystal device using the compound or the composition. SOLUTION: The liquid crystal compound is represented by formula (I). In formula (I), R1 represents H, an alkyl having 1 to 10 carbon atoms, or the like; R2 represents an alkenyl having 2 to 10 carbon atoms or a fluoroalkenyl having 2 to 10 carbon atoms and one or two non-adjacent -CH2- in R2 is replaced by -O- or an ether having 2 to 10 carbon atoms; A1 to A4 each independently represent a formula below, where R3 independently represents H or a halogen; Z1 to Z3 each independently represents a sing bond, -CH2-, -CH2O-, -OCH2-, -CF=CF-, -COO-, -OCO-, -CF2O-, -OCF2-, -C≡C-, -CH=CH-, or the like; and n and m each independently represent 0 or 1. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
- -
-
Paragraph 0036; 0039
(2016/10/07)
-
- HISTONE DEMETHYLASE INHIBITORS
-
Provided herein are substituted pyrazolylpyridine, pyrazolylpyridazine, and pyrazolylpyrimidine derivative compounds and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful for inhibition histone demethylase. Furthermore, the subject compounds and compositions are useful for the treatment of cancer, such as prostate cancer, breast cancer, bladder cancer, lung cancer and/or melanoma and the like.
- -
-
Paragraph 00754; 00755
(2014/06/24)
-
- C-ARYL GLUCOSIDE DERIVATIVES, PREPARATION PROCESS AND PHARMACEUTICAL USE THEREOF
-
C-aryl glucoside derivatives, preparation processes and pharmaceutical uses thereof are disclosed. In particular, C-aryl glucoside derivatives represented by formula (I), with each substituent defined in the application, pharmaceutically acceptable salts or stereoisomers thereof, their preparation methods, and pharmaceutical compositions containing the derivatives as well as their uses as therapeutic agents, particularly as sodium-dependent glucose cotransporter (SGLT)-1 inhibitors, are disclosed.
- -
-
Paragraph 0165
(2013/06/04)
-
- Preparation of [3H]fluoroethyl tosylate and its use in the labelling of the dopamine transporter radioligand [3H]FE-PE2I
-
[3H]Fluoroethyl tosylate, a novel alkylating tritium labelling agent, was synthesized from tritium gas with high specific activity and with 99% radiochemical purity. [3H]Fluoroethyl tosylate was applied in the tritium labelling of the dopamine transporter radioligand [3H]FE- PE2I. Copyright
- Cochrane, Alison R.,Kerr, William John,Sandell, Johan
-
p. 447 - 450
(2014/03/21)
-
- Microwave-assisted synthesis of some novel 1,2,3-triazoles by click chemistry, and their biological activity
-
Five mandipropamid analogues were designed and synthesized via "click chemistry". The phenyl ring of mandipropamid was substituted by a 1,2,3-triazole functional group. Bioassay results indicated that some of the title compounds had moderate fungicidal activity.
- Su, Na-Na,Li, Yao,Yu, Shu-Jing,Zhang, Xiao,Liu, Xing-Hai,Zhao, Wei-Guang
-
p. 759 - 766
(2013/07/27)
-
- 4-(SUBSTITUTED ANILINO)QUINAZOLINE DERIVATIVES AS TYROSINE KINASE INHIBITORS
-
The present invention relates to 4-(substituted anilino)-quinazoline derivatives as tyrosine kinase inhibitors. Specifically, compounds of formula I, or pharmaceutically acceptable salts or solvates thereof are disclosed, in which each substitutent in formula I is defined in the description. Preparation method of the compounds of formula I, pharmaceutical compositons and pharmaceutical uses thereof are also disclosed. The compounds of formula I are effective tyrosine kinase inhibitors.
- -
-
Page/Page column 20
(2012/08/14)
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- 4-(Substituted Anilino)-Quinazoline Derivatives Useful as Tyrosine Kinase Inhibitors
-
The present invention relates to 4-(substituted anilino)-quinazoline derivatives as tyrosine kinase inhibitors. Specifically, compounds of formula I, or pharmaceutically acceptable salts or solvates thereof are disclosed, in which each substitutent in formula I is defined in the description. Preparation method of the compounds of formula I, pharmaceutical compositions and pharmaceutical uses thereof are also disclosed. The compounds of formula I are effective tyrosine kinase inhibitors.
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Page/Page column 14
(2012/08/28)
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- Direct, nucleophilic radiosynthesis of [18F]trifluoroalkyl tosylates: Improved labelling procedures
-
A rapid and efficient protocol to afford the title compound 2-[ 18F]-fluoro-2,2-difluoroethyl tosylate ([18F]7b) is described. Starting from [18F]fluoride ion, labelling reagent 7b was obtained in good yields and a high specific radioactivity. Compound ([ 18F]7b) was then used to synthesise a prospective radiotracer for PET-imaging in dementia.
- Riss, Patrick J.,Ferrari, Valentina,Brichard, Laurent,Burke, Paul,Smith, Robert,Aigbirhio, Franklin I.
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p. 6980 - 6986,7
(2012/12/12)
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- METALLOENZYME INHIBITOR COMPOUNDS
-
The instant invention describes compounds having metalloenzyme modulating activity, and methods of treating diseases, disorders or symptoms thereof mediated by such metalloenzymes.
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-
Page/Page column 26-27
(2013/02/28)
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- METALLOENZYME INHIBITOR COMPOUNDS
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The instant invention describes compounds having metalloenzyme modulating activity, and methods of treating diseases, disorders or symptoms thereof mediated by such metalloenzymes.
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-
Page/Page column 24
(2013/02/28)
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- METALLOENZYME INHIBITOR COMPOUNDS
-
The instant invention describes compounds having metalloenzyme modulating activity, and methods of treating diseases, disorders or symptoms thereof mediated by such metalloenzymes.
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-
Page/Page column 75-76
(2013/02/28)
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- A simple, rapid procedure for nucleophilic radiosynthesis of aliphatic [18F]trifluoromethyl groups
-
A procedure for the radiosynthesis of aliphatic [18F] trifluoromethyl groups by reacting 1,1-difluorovinyl precursors with [ 18F]fluoride ions, resulting in the equivalent of direct nucleophilic addition of H[18F]F, has been developed. A variety of 18F-labelled model compounds were then obtained and two potential [18F]radiotracers were synthesised by a two step process starting from 1,1-difluorovin-2-yl 4-toluenesulfonate. The method is widely applicable for the synthesis of novel radiotracers in high radiochemical yields and good specific activity.
- Riss, Patrick J.,Aigbirhio, Franklin I.
-
supporting information; experimental part
p. 11873 - 11875
(2011/12/04)
-
- Profiling sulfonate ester stability: Identification of complementary protecting groups for sulfonates
-
(Figure presented) Sulfonation is prized for its ability to impart water-solubility to hydrophobic molecules such as dyes. This modification is usually performed as a final step, since sulfonated molecules are poorly soluble in most organic solvents, which complicates their synthesis and purification. This work compares the intrinsic lability of different sulfonate esters, identifying new sulfonate protecting groups and mild, selective cleavage conditions.
- Miller, Stephen C.
-
supporting information; experimental part
p. 4632 - 4635
(2010/09/17)
-
- INHIBITORS OF ACETYL-COA CARBOXYLASE
-
The present invention relates to compounds that act as acetyl-CoA carboxylase (ACC) inhibitors. The invention also relates to methods of preparing the compounds, compositions containing the compounds, and to methods of treatment using the compounds.
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-
Page/Page column 41; 42
(2010/11/17)
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- INHIBITORS OF ACETYL-COA CARBOXYLASE
-
The present invention relates to compounds that act as acetyl-CoA carboxylase (ACC) inhibitors. The invention also relates to methods of preparing the compounds, compositions containing the compounds, and to methods of treatment using the compounds.
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Page/Page column 59
(2010/11/17)
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- The SN3-SN2 spectrum. Rate constants and product selectivities for solvolyses of benzenesulfonyl chlorides in aqueous alcohols
-
Rate constants for a wide range of binary aqueous mixtures and product selectivities (S) in ethanol - Water (EW) and methanol-water (MW) mixtures, are reported at 25 °C for solvolyses of benzenesulfonyl chloride and the 4-chloro - Derivative. S is defined as follows using molar concentrations: S =([ester product]/[acid product]) × ([water solvent]/[alcohol solvent]). Additional selectivity data are reported for solvolyses of 4-Z-substituted sulfonyl chlorides (Z - OMe, Me, H, Cl and NO2) in 2, 2, 2-trifluoroethanol-water. To explain these results and previously published data on kinetic solvent isotope effects (KSIEs) and on other solvolyses of 4-nitro and 4-methoxybenzenesulfonyl chloride, a mechanistic spectrum involving a change from third order to second order is proposed. The molecularity of these reactions is discussed, along with new term 'SN3-SN2 spectrum' and its connection with the better established term 'S N2-SN1 spectrum'. Copyright
- Bentley, T. William,Jones, Robert O,Kang, Dae Ho,Koo, Sun
-
scheme or table
p. 799 - 806
(2010/06/16)
-
- Amphiphilic organocatalyst for schotten-baumann-type tosylation of alcohols under organic solvent free condition
-
A Tosylation of primary alcohol with tosyl chloride was performed effectively with an W-hexadecylimidazole catalyst in water containing K 2CO3 aggregation of the catalyst carrying a hydrophobic methylene chain worked as a substitute for organic solvent.
- Asano, Keisuke,Matsubara, Seijiro
-
supporting information; experimental part
p. 1757 - 1759
(2009/09/06)
-
- Direct vinylation and difluorovinylation of arylboronic acids using vinyl- and 2,2-difluorovinyl tosylates via the Suzuki-Miyaura cross coupling
-
(Chemical Equation Presented) General reaction conditions were developed for the Pd(0)-catalyzed Suzuki-Miyaura coupling reaction of aryl boronic acids with a simple electrophilic vinylation reagent, vinyl tosylate, providing access to styrene derivatives in good yields. The easily accessible vinyl tosylate represents a stable and less toxic alternative to the vinyl halides and the triflate/nonaflate derivatives. Furthermore, this methodology was expanded to provide a facile and straightforward approach for the introduction of a gem-difluorovinyl substituent onto an aromatic ring using the similar and also readily available 2,2-difluorovinyl tosylate as the electrophilic complement.
- Gogsig, Thomas M.,Sobjerg, Lina S.,Lindhardt, Anders T.,Jensen, Kim L.,Skrydstrup, Troels
-
p. 3404 - 3410
(2008/09/21)
-
- PROCESS FOR PREPARING FLUORINE-CONTAINING ALKOXYALKANE
-
A process for preparing a fluorine-containing alkoxyalkane represented by the general formula (1) R1—O—R2—O—R3 where at least one of R1, R2 and R3 contains one or more fluorine atoms. An alcohol with the highest acidity selected from the group consisting of the compounds represented by the general formula (2) R1—OH, the general formula (3) R3—O—R2—OH, the general formula (4) R1—O—R2—OH, and the general formula (5) R3—OH is reacted with at least one selected from the group consisting of the compounds represented by the general formula (6) Lg-R2—O—R3, the general formula (7) Lg-R1, the general formula (8) Lg-R3, and the general formula (9) Lg-R2—O—R1 where Lg represents an anionic leaving group in the presence of a basic compound.
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Page/Page column 7
(2009/01/20)
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- DRUG ADHERENCE MONITORING SYSTEM
-
The present invention provides novel methods for monitoring subject adherence in taking prescribed drugs by detecting markers in exhaled breath after a subject takes the prescribed drug. In particular, the present invention provides novel methods for making additives that are combined with the drug(s). Upon biological breakdown of the drug/additive formulation in a subject's body, markers resulting directly from the biological breakdown of the additives are detected in exhaled breath using sensor technology. In certain embodiments of the invention, the drug adherence monitoring systems and methods include a reporting system capable of tracking subject compliance (either remotely or proximately) and of providing necessary alerts to the subject, caregiver, healthcare provider, and the like.
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Page/Page column 58; 59; 61; 62; Sheet 2
(2010/11/28)
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- SULFONYL-SUBSTITUTED BICYCLIC COMPOUNDS AS MODULATORS OF PPAR
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Compounds as modulators of peroxisome proliferator activated receptors, pharmaceutical compositions comprising the same, and methods of treating disease using the same are disclosed.
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Page/Page column 98-99
(2015/10/07)
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- Scavenger assisted combinatorial process for preparing libraries of tertiary amine compounds
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This invention relates to a novel solution phase process for the preparation of tertiary amine combinatorial libraries. These libraries have utility for drug discovery and are used to form wellplate components of novel assay kits.
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- Novel trifluoroethyliodonium salts from cyclic enaminones and their thermal decomposition
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Upon reaction of 1-[hydroxy(tosyloxy)iodo]-2,2,2-trifluoroethane with cyclic enaminones, stable iodonium tosylates are obtained. Their mild thermolysis provides iodoenaminones and 2,2,2-trifluoroethyl tosylate.
- Papoutsis, Ioannis,Spyroudis, Spyros,Varvoglis, Anastasios,Callies, Jeffrey A.,Zhdankin, Viktor V.
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p. 8401 - 8404
(2007/10/03)
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- Synthesis of alkyl perfluoroalkanedithiocarboxylates and some aspects of their reactivity in cycloaddition reactions
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A new method for the synthesis of the title compounds is proposed.The starting fluorinated compounds are commercially available trifluoroethanol and higher homologues, which were transformed in three steps into (2,2-dichloroperfluoroalkyl) alkylsulfides.The last step consisted in a substitution of chlorine by sulfur by treatment with zinc sulfide.The source of zinc sulfide is crucial and the possible role of catalytic impurities was investigated.These dithioesters are excellent dienophiles.Some cycloaddition reactions with 2,3-dimethylbuta-1,3-diene and 1-(trimethylsilyloxy)buta-1,3-diene are reported. - Keywords: perfluorinated dithioester; polyfluorinated sulfide; cycloaddition; tetrahydrothiopyran
- Portella, Charles,Shermolovich, Yuri G.,Tschenn, Olivier
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p. 697 - 702
(2007/10/03)
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- Various synthetic approaches to fluoroalkyl p-nitrophenyl ethers
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Homologous 1H,1H-perfluoroalkyl p-nitrophenyl ethers (alkyl = C2-C8) were synthesized using different methods. The results are discussed in context with contradictory comments of the literature. The fluoroalkoxylation of p-chloronitrobenzene occurs in only one step, but it is limited to small fluoroalkyl groups. The fluoroalkylation of p-nitrophenol via sulphonic acid esters is a better synthetic route. Differences in reactivity and yield between tosylates, mesylates and inflates are found and discussed. The preferred synthesis includes the use of trifluoromethane sulphonic acid esters.
- Preschera, Dietrich,Thiele, Thomas,Ruhmann, Ralf
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p. 145 - 148
(2007/10/03)
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- Solvolysis of Benzyl Azoxytosylate and the Effect of Added Bases and Nucleophiles in Aqueous Trifluoroethanol and Aqueous Acetonitrile
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The rates and products of reaction of benzyl azoxytosylate (1b) in 1:1 (v/v) aqueous trifluoroethanol containing sodium perchlorate, sodium thiocyanate, sodium iodide, sodium bromide, sodium chloride, sodium hydroxide, sodium acetate, perchloric acid, and imidazole (buffered and unbuffered) have been measured at 42 deg C as part of an investigation into its mechanism of solvolysis.Nonbasic solutes give only small rate effects (some rate enhancing, others rate retarding), but, if nucleophilic, they lead to substitution products-the classic evidence of an SN1 reaction mechanism.After the initial rate-determining fragmentation, about half of the total solvolytic reaction proceeds through an electrophilic benzylic intermediate which is sufficiently long-lived to be trapped by nucleophilic solutes such as thiocyanate and the halide anions to give benzyl thiocyanate and benzyl halides.The other half gives the solvent-derived products benzyl alcohol and benzyl trifluoroethyl ether by a route which is not affected by dilute nonbasic solutes.Sodium acetate, which leads to negligible formation of benzyl acetate, and imidazole lead to the formation of trifluoroethyl tosylate; imidazole also produces N-tosylimidazole.These two base-induced bimolecular reactions involve nucleophilic attack at the sulfur of the tosyl group and involve electronic polarization of 1b in the opposite sense from that in the unimolecular fragmentation.One of the minor products in the presence of bases from the trappable intermediate of the solvolysis reaction is benzaldehyde, which suggests that the intermediate is C6H5CH2ON2+, a new type of reactive electrophile.It is not yet certain whether the half of the unimolecular fragmentation reaction which does not proceed through the trappable intermediate involves another electrophilic intermediate which is simply too short-lived to be intercepted by dilute nucleophiles or whether about half of the initial fragmentation is followed by a concerted uncoupled capture of the nascent benzyl cation by solvent.Replacing a small proportion of the trifluoroethanol in the reaction medium by the more nucleophilic ethanol does not have a drastic effect upon the overall course of the reaction, and a very similar mechanism also appears to be operative in aqueous acetonitrile.
- Maskill, H.,Jencks, William P.
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p. 2062 - 2070
(2007/10/02)
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- Concurrent Solvolytic and Non-solvolytic Reactions of Benzyl Azoxytoluene-p-sulphonate in Aqueous Trifluoroethanol containing Bases: An Unprecedented Mechanistic Duality
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Benzyl azoxytoluene-p-sulphonate (1) undergoes heterolytic fragmentation on solvolysis with the anticipated electron flow from benzyl towards the toluene-p-sulphonate leaving group, but suffers concurrent nucleophilic attack by basic solutes at the sulphur atom of the toluene-p-sulphonate moiety with consequent heterolysis and electron flow in the opposite sense, the benzylazoxy group now being the nucleofuge.
- Maskill, H.
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p. 1433 - 1435
(2007/10/02)
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- SYNTHESIS OF THREE PARTIALLY FLUORINATED ALKANESULFONIC ACIDS AS POTENTIAL FUEL-CELL ELECTROLYTES.
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The simple and effective syntheses of CH//2FCH//2SO//3H, CF//3CH//2SO//3H, AND CHF//2CF//2CH//2SO//3H have been achieved with 18. 8%, 34. 1%, and 33. 7% overall yields. The low molecuar weight partially fluorinated alkanesulfonic acids containing alpha -methylene groups can be prepared from the p-toluenesulfonates of the corresponding alcohols, via a reaction with benzyl mercaptan, followed by an oxidative chlorination of the resulting sulfides, with subsequent hydrolysis of the sulfonyl chloride. The reaction of partially fluorinated alkyl halides with sodium sulfite (Strecker's method) proved to be inefficient (very low yields) and unreliable. The sulfonate salts formed are difficult to recover and purify.
- Bunyagidj,Piotrowska,Aldridge
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p. 344 - 346
(2007/10/02)
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