155136-54-2

Basic information

• Product Name: 3-Pyridinecarbonyl chloride, 4-methyl- (9CI)
• Synonyms: 3-Pyridinecarbonyl chloride, 4-methyl- (9CI);4-Methylpyridine-3-carbonyl chloride
• CAS NO: 155136-54-2
• Molecular Formula: C₇H₆ClNO
• Molecular Weight: 155.58164
• Product Categories: ACIDHALIDE
• Mol File: 155136-54-2.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Pyridinecarbonyl chloride, 4-methyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Pyridinecarbonyl chloride, 4-methyl- (9CI)(155136-54-2)
• EPA Substance Registry System: 3-Pyridinecarbonyl chloride, 4-methyl- (9CI)(155136-54-2)

Safety Data

• Hazardous Substances Data: 155136-54-2(Hazardous Substances Data)

Upstream product

• 3222-50-2 4-methylnicotinic acid 
• 68981-84-0 3-(4',4'-dimethyl-4',5'-dihydro-oxazol-2'-yl)-4-methylpyridine 
• 68981-86-2 3-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)pyridine 
• 94015-05-1 4-methylpyridine-3-carboxylic acid hydrochloride 

Downstream Products

• 669087-32-5 methyl 3-(3-methoxyphenyl)-3-{(4-methylbenzyl)[(4-methyl-3-pyridinyl)carbonyl]amino}propanoate 
• 953067-79-3 N-(3-chlorophenyl)-N-((7,8-difluoro-2-oxo-1,2-dihydroquinolin-4-yl)methyl)-4-methylnicotinamide 
• 953066-26-7 N-(3-chlorophenyl)-N-((8-fluoro-2-oxo-1,2-dihydroquinolin-4-yl)methyl)-4-methylnicotinamide 
• 1350809-30-1 C₂₃H₃₀N₄O 

Relevant articles and documents

Cholinergic agents: Effect of methyl substitution in a series of arecoline derivatives on binding to muscarinic acetylcholine receptors

Arecoline, arecaidine, and a series of derivatives, differing by the presence or absence of methyl groups at positions on the periphery of the molecule, were prepared, and their binding to muscarinic acetylcholine receptors was tested. On the basis of this study, muscarinic agonism for arecoline series is governed by strict structure-activity relationships, as previously observed for other agonist series. Only minor changes in nitrogen substitution were tolerated in the present series of arecoline derivatives.

Improved synthesis of sterically encumbered heteroaromatic biaryls from aromatic β-keto esters

A protocol for the synthesis of hindered 4-aryl 2-aminopyrimidines from β–keto esters is described. The process employs trifluoroethanol as an essential additive to promote the guanidine condensation reaction, enabling the synthesis of 25 aryl- and heteroaryl substituted aminopyrimidines in good yields and high purities with no column chromatography. The conditions described herein are readily scalable and have been employed in the large-scale synthesis of the clinical A2a/A2bR antagonist AB928.

(+)-(2R,5S)-4-[4-cyano-3-(trifluoromethyl)phenyl]-2,5-dimethyl-N-[6- (trifluoromethyl)pyridin-3-yl]piperazine-1-carboxamide (YM580) as an orally potent and peripherally selective nonsteroidal androgen receptor antagonist

A novel series of trans-N-aryl-2,5-dimethylpiperazine-1-carboxamide derivatives was synthesized and their androgen receptor (AR) antagonist activities and in vivo antiandrogenic effects were evaluated. Pharmacological assays indicated that compound 33 was a potent AR antagonist, and subsequent optical resolution provided (+)-(2R,5S)4-[4-cyano-3-(trifluoromethyl)phenyl]-2, 5-dimethyl-N-[6(triflouromethyl)pyridin-3-yl]piperazine-1-carboxamide (33a, YM580) which exhibited the most potent antiandrogenic activity. Unlike bicalutamide, compound 33a decreased the weight of rat ventral prostate in a dose-dependent manner (ED50 = 2.2 mg/kg/day), and induced the maximum antiandrogenic effect, comparable to that of surgical castration, without significantly affecting serum testosterone levels. Compound 33a is a promising clinical candidate for prostate cancer monotherapy.