444665-44-5

Basic information

• Product Name: 1,6-Naphthyridin-2(1H)-one, 1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-
• CAS NO: 444665-44-5
• Molecular Formula: C20H10Cl2F2N2O
• Molecular Weight: 403.215
• Mol File: 444665-44-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1,6-Naphthyridin-2(1H)-one, 1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-Naphthyridin-2(1H)-one, 1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-(444665-44-5)
• EPA Substance Registry System: 1,6-Naphthyridin-2(1H)-one, 1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-(444665-44-5)

Safety Data

• Hazardous Substances Data: 444665-44-5(Hazardous Substances Data)

Upstream product

• 916203-59-3 5-chloro-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one 
• 144025-03-6 2,4-difluorophenylboronic acid 
• 37511-45-8 N-2,6-dichlorophenyl-acrylamide 
• 14432-12-3 4-Amino-2-chloropyridine 
• 73583-37-6 2-chloro-4-bromopyridine 
• 916203-52-6 4-bromo-2-chloro-3-iodo-pyridine 

Downstream Products

• 913556-82-8 1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-1,6-naphthyridin-2(1H)-one 6-oxide 
• 872973-93-8 7-chloro-1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-1,6-naphthyridin-2-(1H)-one 

Relevant articles and documents

Synthesis of a naphthyridone p38 MAP kinase inhibitor

Compound 1 is a p38 MAP kinase inhibitor potentially useful for the treatment of rheumatoid arthritis and psoriasis. A novel six-step synthesis suitable for large-scale preparation was developed in support of a drug development program at Merck Research Laboratories. The key steps include a tandem Heck-lactamization, N-oxidation, and a highly chemoselective Grignard addition of 4-(N-tert-butylpiperidinyl)-magnesium chloride to a naphthyridone N-oxide. The N-oxide exerted complete chemoselectivity via chelation in directing the Grignard addition to the α position as opposed to 1,4-addition on the enelactam. The dihydropyridyl adduct was in situ aromatized with isobutylchloroformate followed by heating in pyridine. Syntheses of Grignard precursor, N-tert-butyl-4-chloro-piperidine, were accomplished via transamination with a quaternary ammonium piperidone or via addition of methylmagnesium chloride to an iminium ion. Utilizing this chemistry, multi-kilogram preparation of compound 1 was successfully demonstrated. American Chemical Society.