cas 7575-93-1, METHYL-D3 P-TOLUENESULFONATE

Articles about 7575-93-1Total 28 be found

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Deuterated compound and application thereof in treatment of cancer
The present invention relates to a deuterated compound and application thereof in the treatment of cancer. Specifically, the present invention provides the compound of formula (I) and pharmaceuticallyacceptable salt or ester thereof, and a pharmaceutical composition thereof. The compound and the pharmaceutical composition are used for inhibiting or regulating the activity of tyrosine kinase and treating disease symptoms or symptoms including cancer mediated by tyrosine kinase.
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Paragraph 0129-0130

(2021/03/06)

Selective C-O Bond Reduction and Borylation of Aryl Ethers Catalyzed by a Rhodium-Aluminum Heterobimetallic Complex
We report the catalytic reduction of a C-O bond and the borylation by a rhodium complex bearing an X-Type PAlP pincer ligand. We have revealed the reaction mechanism based on the characterization of the reaction intermediate and deuterium-labeling experiments. Notably, this novel catalytic system shows steric-hindrance-dependent chemoselectivity that is distinct from conventional Ni-based catalysts and suggests a new strategy for selective C-O bond activation by heterobimetallic catalysis.
Hara, Naofumi,Nakao, Yoshiaki,Saito, Teruhiko,Seki, Rin
supporting information
p. 6388 - 6394
(2021/05/31)

Deuterated substituted butenamide and preparation method and application thereof
The invention belongs to the field of medicines, and particularly relates to deuterated substituted butenamide and a preparation method and application thereof. The deuterated substituted butenamide is prepared from the intermediate compound shown V. Compared with the prior art, the deuterated substituted butenamide is used. The deuterated substituted butane acetamide - N - oxide has a good anti-cancer effect, and the application prospect of the medicine is increased for anti-cancer treatment drugs. , The deuterated substituted butanamide and the deuterated substituted butane acetamide - N - oxide are prepared by the process, the operation is simple, the purity is high, the three wastes are few, and the process is environment-friendly and friendly.
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Paragraph 0175-0177

(2021/10/13)

Regiodivergent DH or HD Addition to Alkenes: Deuterohydrogenation versus Hydrodeuterogenation
The regioselective and regiodivergent addition of H-D to a variety of 1,1-diarylalkenes was realized utilizing selectively deuterated dihydroaromatic compounds, which were generated by cobalt catalysis. The reaction was initiated by catalytic amounts of B
Hilt, Gerhard,Li, Luomo
supporting information

(2020/03/03)

Construction of Biaryls from Aryl Sulfoxides and Anilines by Means of a Sigmatropic Rearrangement
An unprecedented S?N variant of the benzidine rearrangement for construction of biaryls has been developed. Aryl sulfoxides underwent dehydrogenative coupling with anilines by successive treatment with trifluoromethanesulfonic anhydride and trifluorometha
Yanagi, Tomoyuki,Nogi, Keisuke,Yorimitsu, Hideki
p. 783 - 787
(2019/11/13)

INDUSTRIAL PROCESS OF MONO-ALKYLATING A PIPERIDINE NITROGEN IN PIPERIDINE DERIVATIVES WITH DEUTERATED-ALKYL
The present invention relates to a method of mono-alkylating a piperidine nitrogen in a piperidine derivative with a deuterated lower-alkyl, which comprises protecting the piperidine nitrogen with an aralkyl protective group, lower-alkylating the piperidine nitrogen with a deuterated-lower-alkylating agent under neutral or basic condition, and then deprotecting the aralkyl protective group.
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Paragraph 0034; 0037

(2019/04/10)

DEUTERATED 3-(4,5-SUBSTITUTED PYRIMIDINAMINE) PHENYL DERIVATIVES AND APPLICATIONS THEREOF
The present invention discloses a type of deuterated 3-(4,5-substituted aminopyrimidine)phenyl derivatives and use thereof. The derivatives are compounds of Formula (I) or pharmaceutically acceptable salts thereof. These compounds or salts thereof can be used for treatment or prevention of diseases or illnesses through certain mutant forms of epidermal growth factor receptors, inhibit the growth of various tumor cells effectively, and inhibit other proteases of EGFR and Her families, they can be used for preparing anti-tumor drugs.
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Paragraph 0061-0064

(2019/06/27)

THYROID HORMONE RECEPTOR AGONISTS AND USES THEREOF
Described herein are methods and compositions for the treatment of conditions, diseases, or disorders associated with thyroid hormone receptor activity. The methods and compositions disclosed herein include the use of at least one thyroid hormone receptor agonist.
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Paragraph 00461

(2020/01/08)

Preparation method and crystal form of deuterated diphenyl amino pyrimidine compound
The present invention discloses a preparation method and a crystal form of a compound shown in the formula (A) and also discloses a pharmaceutical composition comprising the crystal form of the compound shown in the formula (A) and a method for treating A
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Paragraph 0332-0035

(2019/04/27)

CRYSTALLINE FORM OF 6-(CYCLOPROPANECARBOXAMIDO)-4-((2-METHOXY-3-(1-METHYL-1H-1,2,4-TRIAZOL-3-YL)PHENYL)AMINO)-N-(METHYL-D3) PYRIDAZINE-3-CARBOXAMIDE
Disclosed is crystalline Form B of 6-(cyclopropanecarboxamido)-4-((2-methoxy-3-(1-methyl-1H-1,2,4-triazol-3-yl)phenyl) amino)-N-(methyl-d3)pyridazine-3-carboxamide. Form B is the HCl salt of a neat crystalline form. Characterization data for Form B are disclosed.
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Page/Page column 21

(2019/12/25)

Preparation deuterated diphenylurea (by machine translation)
The invention relates to a method for preparing deuterated diphenyl urea. Specifically, the invention provides an intermediate N-(1, 1, 1-3 deuterated methyl) benzo succinimide which can be used for preparing a deuterated diphenyl urea compound and an application of the intermediate in the preparation of the deuterated diphenyl urea compound. The method can be used for conveniently preparing the intermediate with the high purity and various deuterated diphenyl urea compounds in high efficiency.
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Paragraph 0117-0121

(2018/12/13)

Copper-Catalyzed Intramolecular Benzylic C-H Amination for the Synthesis of Isoindolinones
A copper-catalyzed intramolecular amination occurs at the benzylic C-H of 2-methylbenzamides to deliver the corresponding isoindolinones of great interest in medicinal chemistry. The mild and abundant MnO2 works well as a terminal oxidant, and the reaction proceeds smoothly under potentially explosive organic peroxide-free conditions. Additionally, the directing-group-dependent divergent mechanisms are proposed: 8-aminoquinoline-containing benzamides include a Cu-mediated organometallic pathway whereas an aminyl radical-promoted Hofmann-Loffler-Freytag (HLF)-type mechanism can be operative in the case of N-naphthyl-substituted substrates.
Yamamoto, Chiaki,Takamatsu, Kazutaka,Hirano, Koji,Miura, Masahiro
p. 7675 - 7684
(2016/09/09)

1 -(CYCLOPENT-2-EN-1 -YL)-3-(2-HYDROXY-3-(ARYLSULFONYL)PHENYL)UREA DERIVATIVES AS CXCR2 INHIBITORS
The invention relates to 1-(3-sulfonylphenyl)-3-(cyclopent-2-en-1-yl)urea derivatives, and their use in treating or preventing diseases and conditions mediated by the CXCR2 receptor. In addition, the invention relates to compositions containing the derivatives and processes for their preparation.
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Page/Page column 73

(2015/12/18)

Efficient, scalable and economical preparation of tris(deuterium)- and 13C-labelled N-methyl-N-nitroso-p-toluenesulfonamide (Diazald) and their conversion to labelled diazomethane
A method for the preparation of multi-gramme quantities of N-methyl-d3-N-nitroso-p-toluenesulfonamide (Diazald-d3) and N-methyl-13C-N-nitroso-p-toluenesulfonamide (Diazald-13C) and their conversion to diazomethane-d2 and diazomethane-13C, respectively, is presented. This approach uses robust and reliable chemistry, and critically, employs readily commercially available and inexpensivemethanol as the label source. Several reactions of labelled diazomethane are also reported, including alkene cyclopropanation, phenolmethylation and α-diazoketone formation, as well as deuteriumscrambling in the preparation of diazomethane-d2 and subsequent methyl esterification of benzoic acid.
Shields, Samuel W.J.,Manthorpe, Jeffrey M.
p. 674 - 679
(2015/01/16)

δ-deuterium isotope effects as probes for transition-state structures of isoprenoid substrates
The biosynthetic pathways to isoprenoid compounds involve transfer of the prenyl moiety in allylic diphosphates to electron-rich (nucleophilic) acceptors. The acceptors can be many types of nucleophiles, while the allylic diphosphates only differ in the number of isoprene units and stereochemistry of the double bonds in the hydrocarbon moieties. Because of the wide range of nucleophilicities of naturally occurring acceptors, the mechanism for prenyltransfer reactions may be dissociative or associative with early to late transition states. We have measured δ-secondary kinetic isotope effects operating through four bonds for substitution reactions with dimethylallyl derivatives bearing deuterated methyl groups at the distal (C3) carbon atom in the double bond under dissociative and associative conditions. Computational studies with density functional theory indicate that the magnitudes of the isotope effects correlate with the extent of bond formation between the allylic moiety and the electron-rich acceptor in the transition state for alkylation and provide insights into the structures of the transition states for associative and dissociative alkylation reactions.
Choi, Seoung-Ryoung,Breugst, Martin,Houk, Kendall N.,Poulter, C. Dale
supporting information
p. 3572 - 3580
(2014/05/06)

Design, synthesis, and biological evaluation of deuterated C-aryl glycoside as a potent and long-acting renal sodium-dependent glucose cotransporter 2 inhibitor for the treatment of type 2 diabetes
SGLT2 inhibitors deuterated at sites susceptible to oxidative metabolism were found to have a slightly longer tmax and half-life (t 1/2), dose-dependent increase in urinary glucose excretion (UGE) in rats, and slightly superior effects on UGE in dogs while retaining similar in vitro inhibitory activities against hSGLT2. In particular, deuterated compound 41 has the potential to be a robust long-acting antidiabetic agent.
Xu, Ge,Lv, Binhua,Roberge, Jacques Y.,Xu, Baihua,Du, Jiyan,Dong, Jiajia,Chen, Yuanwei,Peng, Kun,Zhang, Lili,Tang, Xinxing,Feng, Yan,Xu, Min,Fu, Wei,Zhang, Wenbin,Zhu, Liangcheng,Deng, Zhongping,Sheng, Zelin,Welihinda, Ajith,Sun, Xun
p. 1236 - 1251
(2014/03/21)

METHOD FOR PREPARING DEUTERATED DIPHENYLUREA
Disclosed are an intermediate compound of N-(1,1,1-trideuterated methyl)phthalimide, and its use in the preparation of deuterated diphenylurea derivative.
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Paragraph 0062-0064

(2013/03/26)

PREPARATION METHODS OF METHYL-D3-AMINE AND SALTS THEREOF
Preparation methods of methyl-d3-amine and salts thereof are provided, which contain the following steps: (i) nitromethane is subjected to react with deuterium oxide in the present of bases and phase-transfer catalysts to form nitromethane-d3, which is subsequently subjected to reduction in an inert solvent to form methyl-d3-amine, and optionally, methyl-d3-amine reacts subsequently with acids to form salts of methyl-d3-amine; or (ii) N-(1,1,1-trideuteriomethyl)phthalimide is subjected to react with acids to form salts of methyl-d3-amine. The present methods are easy, high efficient, and low cost.
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Paragraph 0060; 0061

(2013/03/26)

METHOD FOR PREPARING DEUTERATED DIPHENYLUREA
Disclosed are an intermediate compound of N-(1,1,1-trideuterated methyl)phthalimide, and its use in the preparation of deuterated diphenylurea derivative.
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Paragraph 0103; 0104

(2013/03/26)

An efficient synthesis of [D6]leucocrystal violet
This report presents an efficient synthesis of [D6]leucocrystal violet. Esterification of p-toluenesulphonyl chloride with [D4]methanol provided [D 3]methyl p-toluenesulphonate, which was used to methylate aniline to give [D6]N, N-di
Yang, Weicheng,Luo, Yong,Liu, Weixia,Deng, Xiaojun,Du, Xiaoning,Li, Meihua
experimental part
p. 211 - 213
(2012/05/20)

DEUTERATED BENZYLBENZENE DERIVATIVES AND METHODS OF USE
Provided are compounds having an inhibitory effect on sodium-dependent glucose cotransporter SGLT. The invention also provides pharmaceutical compositions, methods of preparing the compounds, synthetic intermediates, and methods of using the compounds, independently or in combination with other therapeutic agents, for treating diseases and conditions that are affected by SGLT inhibition.
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Page/Page column 155; 156

(2010/04/03)

Elucidating the transformation pattern of the cereal allelochemical 6-methoxy-2-benzoxazolinone (MBOA) and the trideuteriomethoxy analogue [D 3]-MBOA in soil
To deduce the structure of the large array of compounds arising from the transformation pathway of 6-methoxybenzoxazolin-2-one (MBOA), the combination of isotopic substitution and liquid chromatography analysis with mass spectrometry detection was used as
Etzerodt, Thomas,Nielsen, Susan T.,Mortensen, Anne G.,Christophersen, Carsten,Fomsgaard, Inge S.
p. 1075 - 1085
(2007/10/03)

Involvement of Diels-Alder reactions in the biosynthesis of secondary natural products: The late stage of the biosynthesis of the phytotoxins solanapyrones
Advanced intermediates, prosolanapyrones I (6) and II (7) have been synthesized in deuterium labelled form and administered to cultures of Alternaria solani. Incorporation of [17,17,18,18,18-2H5]prosolanapyrone I (6b) afforded solana
Oikawa, Hideaki,Suzuki, Yuichi,Katayama, Kinya,Naya, Akira,Sakano, Chiaki,Ichihara, Akitami
p. 1225 - 1232
(2011/05/18)

Ester Cleavage in Superacid Media Involving Diprotonated Gitonic Carboxonium Dications
The reactivity of protonated and methylated methyl ester in superacidic media was investigated by experiment and theory.Protonated methyl acetate was found to undergo slow acyl oxygen cleavage at -78 deg C in FSO3H/SbF5/SO2 solution to give acetyl cation and methyloxonium ion. 1,1-Dimethoxyethyl cation (methylated methyl acetate) was found to undergo slow methyl exchange in CD3SO3F/SbF5 solution.The reaction of 1,1-dimethoxyethyl cation with toluene in the presence of trifluoromethanesulfonic acid at -78 deg C gave acylation in 4percent yield.Theoretical calculations at the MP4(SDTQ)/6-31G*//MP2/6-31G* level of theory were performed to find stationary points on the potential energy surface of the mono- and diactivated ester system.Based on the available evidence a new mechanism for the acid-catalyzed ester cleavage in superacidic media is proposed.
Olah, George A.,Hartz, Nikolai,Rasul, Golam,Burrichter, Arwed,Prakash, G. K. Surya
p. 6421 - 6427
(2011/05/18)

Effect on conformation on proton affinities of stereoisomeric ethers
The proton affinity (PA) of cis-4-tert-butylcyclohexyl methyl ether with an axial methoxy group is higher by ~ 0.1 kcal mol-1 (1 kcal = 4.184 kJ) than the trans isomer with the equatorial ether group. The gas-phase basicity shows a similar smal
Denekamp,Etinger,Fokkens,Khaselev,Mandelbaum,Nibbering
p. 1174 - 1178
(2007/10/03)

Substituent Effects on Transition-state Structures for Dissociative and Associative SN2 Reactions
α-Deuterium secondary kinetic isotope effects (KIEs) have been investigated for the reactions of anilines with benzyl, methyl and ethyl benzenesulfonates involving deuteriated aniline nucleophiles and substrates.The secondary KIEs observed are normal, kH/kD > 1.0, only for the deuteriated benzyl system and are of an inverse type, kH/kD N2 mechanism), in contrast to the reverse trend, i.e., the strain incurred by bond formation of the nucleophile is greater than the relief of steric congestion by bond breaking of the leaving group in the reactions of alkyl compounds (associative SN2 mechanism).The effects of substituents in the nucleophile (X) and leaving group (Z) on the secondary KIEs are in complete agreement with the transition-state variation predicted by the sign and magnitude of the cross-interaction constant, ρxz.
Lee, Ikchoon,Koh, Han Joong,Lee, Bon-Su,Sohn, Dong Sook,Lee, Byung Choon
p. 1741 - 1746
(2007/10/02)

Chemical Consequences of the Intramolecular Interaction between a Sulphur Atom and a Methoxycarbonyl Group in Fluorene Systems
The intramolecular interaction between a sulphur atom and a methoxycarbonyl group was found to affect their chemical reactivity.The rates of C-S bond cleavage in methyl-9,9-bis(ethylthio)fluorene-x-carboxylate, where x is 1, 2, or 3, with sodium ethanethiolate show that the rate is minimal, though comparable with the others, when x=1, because of steric effects.In contrast, methyl 9-(ethylthio)fluorene-x-carboxylates, where x=1, 2, or 3, exhibit the maximum rate when x=1.The rates of ester exchange in the presence of toluene-p-sulphonic acid indicate that the reaction is accelerated by the presence of two ethylthio groups at the 9 position of methyl fluorene-1-carboxylate but no significant effect is detected if there is only one ethylthio group.The hydrolysis of the thioketal group in 9,9-bis(ethylthio)fluorene is also accelerated by the presence of a 1-methoxycarbonyl group.The implication of these results are discussed with the use of a model compound.
Nakanishi, Waro,Kusuyama, Yoshiaki,Ikeda, Yoshitsugu,Oki, Michinori
p. 799 - 804
(2007/10/02)

Synthesis and Photolysis of 1,4-Dialkyl-1,4-dihydro-5H-tetrazol-5-ones and -thiones. A Novel Approach to Diaziridinones and Carbodiimides
The regioselective alkylation of the 1-tert-butyl-1,4-dihydro-5H-tetrazol-5-one (7) produced the 1,4-dialkyltetrazolones 8b and c.The electron impact induced decomposition of the known, most simple tetrazolone 8a proceeded via a cycloelimination into methyl azide and methyl isocyanate.On photolysis in acetonitrile or pentane, the tetrazolones 8 lost nitrogen and formed 1,2-dialkyldiaziridinones 24, of which 24c was isolated in pure form.Very reactive alkylating reagents, e.g. methyl fluorosulfonate, trimethyloxonium tetrafluoroborate, or tert-butyl alcohol/tetrafluoroboric acid in ether, preferentially alkylated N-3 of 1-methyl-5-(methylthio)-1H-tetrazole (9a); dimethyl sulfate reacted almost equally at N-3 or N-4.In the mixture of the salts 10a and 11a obtained in this way, only 11a was demethylated at the sulfur atom by triethylamine in acetonitrile affording the easily separable tetrazolethione 5a.Diazomethane methylated 1-tert-butyl-1,4-dihydro-5H-tetrazole-5-thione (18b) predominantly at the sulfur atom.In contrast, 2-diazopropane gave approximately equal fractions of S-alkylation and N-4-alkylation producing the tetrazolethione 5c.Besides fragment ions resulting from cycloelimination products, in the electron impact induced decomposition of the most simple tetrazolethione 5a, ions were observed which correspond to loss of nitrogen from the molecular ion.On photolysis in alkanes or acetonitrile in the temperature range between +20 and -40 deg C the tetrazolethiones lost nitrogen furnishing high yields of sulfur and the carbodiimides 30.
Quast, Helmut,Bieber, Lothar
p. 3253 - 3272
(2007/10/02)