1093951-85-9

Basic information

• Product Name: 5-(methyl-d3)-1-phenylpyridin-2(1H)-one
• Synonyms: 5-(methyl-d3)-1-phenylpyridin-2(1H)-one
• CAS NO: 1093951-85-9
• Molecular Weight: 188.202
• Mol File: 1093951-85-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 5-(methyl-d3)-1-phenylpyridin-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(methyl-d3)-1-phenylpyridin-2(1H)-one(1093951-85-9)
• EPA Substance Registry System: 5-(methyl-d3)-1-phenylpyridin-2(1H)-one(1093951-85-9)

Safety Data

• Hazardous Substances Data: 1093951-85-9(Hazardous Substances Data)

Upstream product

• 1132025-49-0 5-(methyl-d3)pyridin-2(1H)-one 
• 98-80-6 phenylboronic acid 
• 13472-85-0 2-methoxy-5-bromopyridine 
• 1132025-51-4 5-(methyl-d3)-2-methoxypyridine 
• 13466-38-1 5-bromopyridin-2(1H)-one 
• 1332481-37-4 (methyl-d₃)boronic acid 
• 77837-08-2 6-oxo-1-phenyl-1,6-dihydro-3-pyridinecarboxylic acid 
• 66171-50-4 6-oxo-1,6-dihydropyridin-3-carboxylic acid methyl ester 
• 591-50-4 iodobenzene 

Relevant articles and documents

A highly efficient Suzuki-Miyaura methylation of pyridines leading to the drug pirfenidone and its CD3 version (SD-560)

Efficient introduction of methyl or methyl-d3 into aromatic and heteroaromatic systems still presents a synthetic challenge. In particular, we were in search of a non-cryogenic synthesis of the 5-CD3 version of pirfenidone (4d, also known as Pirespa, Esbriet or Pirfenex), one of the two drugs approved to date for retarding idiopathic pulmonary fibrosis (IPF), a serious, rare and fatal lung disease, with a life expectancy of 3-5 years. The methyl-deuterated version of pirfenidone (4e, also known as SD-560) was designed with the objective of attenuating the rate of drug metabolism, and our goal was to find a green methylation route to avoid the environmental and economic impact of employing alkyllithium at cryogenic temperatures. The examination of several cross-coupling strategies for the introduction of methyl or methyl-d3 into methoxypyridine and pyridone systems culminated in two green and nearly quantitative Suzuki-Miyaura cross-coupling routes in the presence of RuPhos ligand: the first, using commercially available methyl boronic acid or its CD3 analog and the second, employing potassium methyl trifluoroborate or CD3BF3K, the latter obtained by a new route in 88% yield. This led, on a scale of tens of grams, to the synthesis of pirfenidone (4d) and its d3 analog, SD-560 (4e), at 99% isotopic purity.

DEUTERATED PIRFENIDONE

This invention relates to novel substituted pyridinones, their derivatives, pharmaceutically acceptable salts, solvates, and hydrates thereof. This invention also provides compositions comprising a compound of this invention and the use of such compositio