cas 5165-28-6, 5,5-Dimethyl-2-pyrrolidinone

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LOW TOXICITY NMP SUBSTITUTES AND USES THEREOF
The present technology is directed to compounds Formulas I, II, III, and IV as well as compositions that include one or more of the compounds and methods of making the compounds. In particular, the present compounds may be used as a replacement for NMP in compositions to produce lower toxicity compositions.
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(2021/08/20)

A class of histone acetylase p300 inhibitors, and application thereof
The invention discloses a class of histone acetylase p300 inhibitors, and application thereof, and belongs to the technical field of medicinal chemistry. The invention discloses a compound representedby a formula (I), or a stereochemical isomer, a solvate or a pharmaceutically acceptable salt thereof. According to the invention, the compound can effectively inhibit the activity of histone acetylase p300 and can effectively inhibit the proliferation activity of various tumor cells; the compound is combined with a CDK4/6 inhibitor to play a synergistic role in inhibiting proliferation of tumorcells; and the compound has good application prospects in preparation of histone acetylase inhibitors, preparation of drugs for preventing and/or treating cancers, metabolic diseases, neurological diseases or inflammations, and combination of drugs.
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Paragraph 0280-0281; 0285-0287

(2020/06/17)

Basicities and Nucleophilicities of Pyrrolidines and Imidazolidinones Used as Organocatalysts
The Br?nsted basicities pKaH (i.e., pKa of the conjugate acids) of 32 pyrrolidines and imidazolidinones, commonly used in organocatalytic reactions, have been determined photometrically in acetonitrile solution using CH acids as indicators. Most investigated pyrrolidines have basicities in the range 16 aH aH aH 12.6) and the 2-imidazoliummethyl-substituted pyrrolidine A21 (pKaH 11.1) are outside the typical range for pyrrolidines with basicities comparable to those of imidazolidinones. Kinetics of the reactions of these 32 organocatalysts with benzhydrylium ions (Ar2CH+) and structurally related quinone methides, common reference electrophiles for quantifying nucleophilic reactivities, have been measured photometrically. Most reactions followed second-order kinetics, first order in amine and first order in electrophile. More complex kinetics were observed for the reactions of imidazolidinones and several pyrrolidines carrying bulky 2-substituents, due to reversibility of the initial attack of the amines at the electrophiles followed by rate-determining deprotonation of the intermediate ammonium ions. In the presence of 2,4,6-collidine or 2,6-di-tert-butyl-4-methyl-pyridine, the deprotonation of the initial adducts became faster, which allowed the rate of the attack of the amines at the electrophiles to be determined. The resulting second-order rate constants k2 followed the correlation log?k2(20 °C) = sN(N + E), where electrophiles are characterized by one parameter (E) and nucleophiles are characterized by the two solvent-dependent parameters N and sN. In this way, the organocatalysts A1-A32 were integrated in our comprehensive nucleophilicity scale, which compares n-, -, and σ-nucleophiles. The nucleophilic reactivities of the title compounds correlate only poorly with their Br?nsted basicities.
An, Feng,Maji, Biplab,Min, Elizabeth,Ofial, Armin R.,Mayr, Herbert
supporting information
p. 1526 - 1547
(2020/02/04)

Photocatalytic Intramolecular C-H Amination Using N-Oxyureas as Nitrene Precursors
Nitrenes are remarkable high-energy chemical species that enable direct C-N bond formation, typically via controlled reactions of metal-stabilized nitrenes. Here, in contrast, the combined use of photocatalysis with careful engineering of the precursor enabled C-H amination forming imidazolidinones and related nitrogen heterocycles from readily accessible hydroxylamine precursors. Preliminary mechanistic results are consistent with the formation of free carbamoyl triplet nitrenes as reactive intermediates.
Ivanovich, Ryan A.,Polat, Dilan E.,Beauchemin, André M.
supporting information
p. 6360 - 6364
(2020/09/02)

Synthesis of Lactams via Ir-Catalyzed C-H Amidation Involving Ir-Nitrene Intermediates
x-membered lactams were synthesized via either an amidation of sp3 C-H bonds or an electrophilic substitution of arenes via Ir-nitrene intermediates. With the employment of a readily available iridium catalyst in dichloromethane or hexafluoro-2-propanol, a wide range of lactams were synthesized in good to excellent yields with high selectivity.
Li, Xiaoxun,Liu, Jitian,Tang, Weiping,Wang, Shuojin,Ye, Wenjing,Zheng, Junrong
(2020/03/19)

Tuning Triplet Energy Transfer of Hydroxamates as the Nitrene Precursor for Intramolecular C(sp3)-H Amidation
Reported herein is the design of a photosensitization strategy to generate triplet nitrenes and its applicability for the intramolecular C-H amidation reactions. Substrate optimization by tuning physical organic parameters according to the proposed energy transfer pathway led us to identify hydroxamates as a convenient nitrene precursor. While more classical nitrene sources, representatively organic azides, were ineffective under the current photosensitization conditions, hydroxamates, which are readily available from alcohols or carboxylic acids, are highly efficient in accessing synthetically valuable 2-oxazolidinones and γ-lactams by visible light. Mechanism studies supported our working hypothesis that the energy transfer path is mainly operative.
Chang, Sukbok,Jung, Hoimin,Keum, Hyeyun,Kweon, Jeonguk
supporting information
p. 5811 - 5818
(2020/04/10)

CDK4/6 INHIBITORS AND USE THEREOF
The present disclosure relates to a compound of formula (I), or a pharmaceutically acceptable salt, a solvate, a stereoisomer, or tautomer thereof, a pharmaceutical composition comprising a compound of formula (A) or formula (B), and any subgenera thereof, and use of said compounds and compositions thereof, wherein R1, R2, R3a, R3b, R5, R6, X1, X2, Y and n are described herein.
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Paragraph 616; 619; 620

(2019/03/05)

Strategic Approach to the Metamorphosis of γ-Lactones to NH γ-Lactams via Reductive Cleavage and C-H Amidation
A new approach has elaborated on the conversion of γ-lactones to the corresponding NH γ-lactams that can serve as γ-lactone bioisosteres. This approach consists of reductive C-O cleavage and an Ir-catalyzed C-H amidation, offering a powerful synthetic tool for accessing a wide range of valuable NH γ-lactam building blocks starting from γ-lactones. The synthetic utility was further demonstrated by the late-stage transformation of complex bioactive molecules and the asymmetric transformation.
Jung, Hoi-Yun,Chang, Sukbok,Hong, Sungwoo
p. 7099 - 7103
(2019/09/07)

AMINO PYRIMIDINE COMPOUND FOR INHIBITING PROTEIN TYROSINE KINASE ACTIVITY
An amino pyrimidine compound for inhibiting protein tyrosine kinase activity, a pharmaceutical composition thereof, preparation therefor, and an application thereof. Specifically, an amino pyrimidine compound represented by formula (I), R1, R2, L, Y, R6, W, A, m, and n being defined in the specification, and a pharmaceutically acceptable salt, a stereoisomer, a solvent compound, a hydrate, a polymorphism, a prodrug, or an isotope variant thereof. The compound can be used for treating and/or preventing protein tyrosine kinase-related diseases such as cell proliferative diseases, cancers, and immune diseases.
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Paragraph 0479; 0480

(2019/06/07)

Synthetic Utility of N-Benzoyloxyamides as an Alternative Precursor of Acylnitrenoids for γ-Lactam Formation
Described herein is the development of a new entry of acylnitrenoid precursors for γ-lactam synthesis via an intramolecular C-H amidation reaction. Upon Ir catalysis, N-benzoyloxyamides serve as efficient substrates to afford 5-membered amides. Mechanistic studies revealed that the generation of a putative Ir-carbonylnitrenoid via N-O bond cleavage is facilitated by the chelation of countercations. This protocol offers a convenient and step-economic route to γ-lactams starting from the corresponding carboxylic acids.
Huh, Soohee,Hong, Seung Youn,Chang, Sukbok
p. 2808 - 2812
(2019/04/17)

Harnessing Secondary Coordination Sphere Interactions That Enable the Selective Amidation of Benzylic C-H Bonds
Engineering site-selectivity is highly desirable especially in C-H functionalization reactions. We report a new catalyst platform that is highly selective for the amidation of benzylic C-H bonds controlled by π-πinteractions in the secondary coordination sphere. Mechanistic understanding of the previously developed iridium catalysts that showed poor regioselectivity gave rise to the recognition that the π-cloud of an aromatic fragment on the substrate can act as a formal directing group through an attractive noncovalent interaction with the bidentate ligand of the catalyst. On the basis of this mechanism-driven strategy, we developed a cationic (ν5-C5H5)Ru(II) catalyst with a neutral polypyridyl ligand to obtain record-setting benzylic selectivity in an intramolecular C-H lactamization in the presence of tertiary C-H bonds at the same distance. Experimental and computational techniques were integrated to identify the origin of this unprecedented benzylic selectivity, and robust linear free energy relationship between solvent polarity index and the measured site-selectivity was found to clearly corroborate that the solvophobic effect drives the selectivity. Generality of the reaction scope and applicability toward versatile γ-lactam synthesis were demonstrated.
Jung, Hoimin,Schrader, Malte,Kim, Dongwook,Baik, Mu-Hyun,Park, Yoonsu,Chang, Sukbok
supporting information
p. 15356 - 15366
(2019/10/22)

Discovery of Tetrahydroisoquinoline-Containing CXCR4 Antagonists with Improved in Vitro ADMET Properties
CXCR4 is a seven-transmembrane receptor expressed by hematopoietic stem cells and progeny, as well as by ≥48 different cancers types. CXCL12, the only chemokine ligand of CXCR4, is secreted within the tumor microenvironment, providing sanctuary for CXCR4+ tumor cells from immune surveillance and chemotherapeutic elimination by (1) stimulating prosurvival signaling and (2) recruiting CXCR4+ immunosuppressive leukocytes. Additionally, distant CXCL12-rich niches attract and support CXCR4+ metastatic growths. Accordingly, CXCR4 antagonists can potentially obstruct CXCR4-mediated prosurvival signaling, recondition the CXCR4+ leukocyte infiltrate from immunosuppressive to immunoreactive, and inhibit CXCR4+ cancer cell metastasis. Current small molecule CXCR4 antagonists suffer from poor oral bioavailability and off-target liabilities. Herein, we report a series of novel tetrahydroisoquinoline-containing CXCR4 antagonists designed to improve intestinal absorption and off-target profiles. Structure-activity relationships regarding CXCR4 potency, intestinal permeability, metabolic stability, and cytochrome P450 inhibition are presented.
Miller, Eric J.,Jecs, Edgars,Truax, Valarie M.,Katzman, Brooke M.,Tahirovic, Yesim A.,Wilson, Robert J.,Kuo, Katie M.,Kim, Michelle B.,Nguyen, Huy H.,Saindane, Manohar T.,Zhao, Huanyu,Wang, Tao,Sum, Chi S.,Cvijic, Mary E.,Schroeder, Gretchen M.,Wilson, Lawrence J.,Liotta, Dennis C.
p. 946 - 979
(2018/02/17)

Selective formation of γ-lactams via C-H amidation enabled by tailored iridium catalysts
Intramolecular insertion of met al nitrenes into carbon-hydrogen bonds to form γ-lactam rings has traditionally been hindered by competing isocyanate formation. We report the application of theory and mechanism studies to optimize a class of pentamethylcyclopentadienyl iridium(III) catalysts for suppression of this competing pathway. Modulation of the stereoelectronic properties of the auxiliary bidentate ligands to be more electron-donating was suggested by density functional theory calculations to lower the C-H insertion barrier favoring the desired reaction. These catalysts transform a wide range of 1,4,2-dioxazol-5-ones, carbonylnitrene precursors easily accessible from carboxylic acids, into the corresponding γ-lactams via sp3 and sp2 C-H amidation with exceptional selectivity. The power of this method was further demonstrated by the successful late-stage functionalization of amino acid derivatives and other bioactive molecules.
Hong, Seung Youn,Park, Yoonsu,Hwang, Yeongyu,Kim, Yeong Bum,Baik, Mu-Hyun,Chang, Sukbok
p. 1016 - 1021
(2018/03/09)

CERTAIN PROTEIN KINASE INHIBITOR
Provided are certain CDK4/6 inhibitors, pharmaceutical compositions thereof, and methods of use therefor.
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Paragraph 267; 268

(2017/01/09)

TYK2 INHIBITORS AND USES THEREOF
The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of TYK2, and the treatment of TYK2-mediated disorders.
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Paragraph 001135; 001136

(2015/09/28)

INHIBITING THE TRANSIENT RECEPTOR POTENTIAL A1 ION CHANNEL
The present invention relates to compounds of the Formula (I), or a pharmaceutically acceptable salt, pharmaceutical preparation, or pharmaceutical composition thereof, and their use for the treatment of pain, inflammatory disease, neuropathy, dermatological disorders, pulmonary conditions, and cough, as well as inhibiting the Transient Receptor Potential Al ion channel (TRPA1).
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Page/Page column 52; 53

(2015/11/16)

NOVEL AMINO-PYRROLINE DERIVATIVES, AND USE THEREOF IN THE PREVENTION AND/OR TREATMENT OF METABOLIC SYNDROME
Novel amino-pyrrolinic derivatives, their pharmacologically acceptable salts and use thereof in the prevention and/or treatment of metabolic syndrome.
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Paragraph 0183; 0184

(2014/03/21)

Preventing thermolysis: Precursor design for volatile copper compounds
A copper(i) iminopyrrolidinate was synthesized and evaluated by thermal gravimetric analysis (TGA), solution based 1H NMR studies and surface chemistry to determine its thermal stability and decomposition mechanism. Copper(i) tert-butyl-imino-2
Coyle, Jason P.,Kurek, Agnieszka,Pallister, Peter J.,Sirianni, Eric R.,Yap, Glenn P. A.,Barry, Sean T.
p. 10440 - 10442
(2012/11/13)

(INDOL-3-YL)-HETEROCYCLE DERIVATIVES AS AGONISTS OF THE CANNABINOID CB1 RECEPTOR
The invention relates to (indol-3-yl)-heterocycle derivatives having general Formula (I) wherein A represents a 5-membered aromatic heterocyclic ring, wherein X1, X2 and X3 are independently selected from N, O, S and CR; R is H or (C1-4)alkyl; or R, when present in X2 or X3, may form together with R3 a 5-8 membered ring; R1 is a 5-8 mem-bered saturated carbocyclic ring, optionally containing a heteroatom selected from O and S; R2 is H, CH3 or CH2-CH3;or R2 is joined together with R7 to form a 6-mem-bered ring, optionally containing a heteroatom selected from O and S, and which heteroatom is bonded to the 7-position of the indole ring; R3 and R4 are independent-ly H, (C1-6)alkyl or (C3-7)cycloalkyl, the alkyl groups being optionally substituted with OH, (C1-4)alkyloxy, (C1-4)alkylthio, (C1-4)alkylsulfonyl, CN or halogen; or R3 together with R4 and the N to which they are bonded form a 4-8 membered ring optionally containing a further heteroatom selected from O and S, and which is optionally sub-stituted with OH, (C1-4)alkyl, (C1-4)alkyloxy, (C1-4)alkyloxy- (C1-4)alkyl, or halogen; or R3 together with R5 forms a 4-8 membered ring optionally containing a further hetero-atom selected from O and S, and which is optionally substituted with OH, (C1-4)alkyl, (C1-4)alkyloxy, (C1-4)alkyloxy- (C1-4)alkyl, or halogen; or R3 together with R, when present in X2 or X3, forms a 5-8 membered ring; R5 is H or (C1-4)alkyl; or R5 together with R3 forms a 4-8 membered ring optionally containing a further heteroatom select-ed from O and S, and which is optionally substituted with OH, (C1-4)alkyl, (C1-4)alkyl-oxy, (C1-4) alkyloxy- (C1-4)alkyl, or halogen; R5' is H or (C1-4)alkyl; R6 represents 1-3 substituents independently selected from H, (C1-4 alkyl, (C1-4) alkyloxy, CN and halogen; R7 is H, (C1-4)alkyl, (C1-4)alkyloxy, CN or halogen; or R7 is joined together with R2 to form a 6-membered ring, optionally containing a further heteroatom selected from O and S, and which heteroatom is bonded to the 7-position of the indole ring; or a pharmaceutically acceptable salt thereof, as agonists of the cannabinoid CB1 receptor, which can be used in the treatment of pain such as for example peri-operative pain, chronic pain, neuropathic pain, cancer pain and pain and spasticity associated with multiple sclerosis.
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Page/Page column 51

(2010/02/14)

Preparation of γ- and δ-lactams by ring closure of β,γ-unsaturated amides using trifluoromethanesulfonic acid
γ-Lactams and δ-lactams can be prepared by the reaction of β,γ-unsaturated amides with trifluoromethanesulfonic acid.
Marson, Charles M.,Fallah, Asad
p. 293 - 296
(2007/10/02)

Synthesis and Photochemistry of 5,5-Dimethyl-1H-pyrrol-2(5H)-one and Some N-Substituted Derivatives
In two steps 5,5-dimethyl-1H-pyrrol-2(5H)-one (3a) was prepared from 5,5-dimethylpyrrolidine-2,4-dione (=dimethyltetramic acid; 4) in 71percent overall yield (Scheme 1) and further converted to N-substituted derivatives 3b-f via acylation, alkylation, or methoxycarbonylation of its anion (Scheme 2).The substituents on the N-atom exert a strong influence on the photochemical reactivity ( photocycloaddition to 2,3-dimethylbut-2-ene, photocyclodimerisation, photoreduction) of these aza-enones 3 (Scheme 3).In general, N-alkyl compounds react much slower and with less efficiency than either the (N-unsubstituted) title compound 3a or its N-acetyl and N-(methoxycarbonyl)derivatives 3e and 3f, respectively.These compounds behave similarly to the corresponding lactone, 5,5-dimethyl-2(5H)-furanone, studied previously.
Ihlefeld, Andreas,Margaretha, Paul
p. 1333 - 1340
(2007/10/02)

α-pyrrolidones and a method for preparation thereof
α-Pyrrolidones and cyclic amidines Ia and Ib, respectively, for washing gases. STR1 where R1 and R2 are each C1 -C8 -alkyl, C1 -C8 -alkoxy, C3 -C10 -cycloalkyl or Csu
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(2008/06/13)

New Reactions of Deoxyvasicinone. Part 4.
Analogues of deoxyvasicinone (1) in which the pyrrolo ring is substituted, enlarged, or attached to the a face of the quinazolone system were prepared and several reactions of these analogues with electrophilic reagents have been investigated.
Dunn, A. D.,Kinnear, K. I.
p. 53 - 57
(2007/10/02)

RAPID AND EFFICIENT REDUCTION OF ALIPHATIC NITRO COMPOUNDS TO AMINES
The combination of NaBH4 with catalytic quantities of NiCl2 smoothly reduces aliphatic nitro compounds to amines in methanol; Ni2B formed in situ is the active catalyst.
Osby, John O.,Ganem, Bruce
p. 6413 - 6416
(2007/10/02)