1224442-80-1

Basic information

• Product Name: (R)-3-(4-fluorophenyl)-2-formylpentanedioic acid 1-methyl ester
• Synonyms: (R)-3-(4-fluorophenyl)-2-formylpentanedioic acid 1-methyl ester
• CAS NO: 1224442-80-1
• Molecular Weight: 268.242
• Mol File: 1224442-80-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (R)-3-(4-fluorophenyl)-2-formylpentanedioic acid 1-methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-(4-fluorophenyl)-2-formylpentanedioic acid 1-methyl ester(1224442-80-1)
• EPA Substance Registry System: (R)-3-(4-fluorophenyl)-2-formylpentanedioic acid 1-methyl ester(1224442-80-1)

Safety Data

• Hazardous Substances Data: 1224442-80-1(Hazardous Substances Data)

Upstream product

• 64-19-7 acetic acid 
• 201230-82-2 carbon monoxide 
• 4926-12-9 4-(4-fluorophenyl)dihydropyran-2,6(3H)-dione 
• 50737-52-5 ethyl 2-cyano-3-(4-fluorophenyl)acrylate 
• 459-57-4 4-fluorobenzaldehyde 
• 3449-63-6 3-(4-fluorophenyl)pentan-1,5-dioic acid 
• 107-31-3 Methyl formate 

Downstream Products

• 1220248-47-4 (S)-4-(4-fluorophenyl)-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylic acid methyl ester 
• 1224442-81-2 (S)-4-(4-fluorophenyl)-1-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylic acid methyl ester 
• 1232685-21-0 (4S)-N-[1-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-5-methyl-indazol-6-yl]-4-(4-fluorophenyl)-2-oxo-3,4-dihydro-1H-pyridine-5-carboxamide 
• 1232506-24-9 (4S)-4-(4-fluorophenyl)-2-oxo-3,4-dihydro-1H-pyridine-5-carbonyl chloride 
• 1232684-78-4 (4S)-4-(4-fluorophenyl)-N-[1-(2-hydroxyethyl)-5-methyl-indazol-6-yl]-2-oxo-3,4-dihydro-1H-pyridine-5-carboxamide 
• 1232503-95-5 (4S)-N-[4-chloro-5-(2-hydroxyethoxy)-2-methyl-phenyl]-4-(4-fluorophenyl)-2-oxo-3,4-dihydro-1H-pyridine-5-carboxamide 

Relevant articles and documents

Novel Series of Dihydropyridinone P2X7 Receptor Antagonists

Identification of singleton P2X7 inhibitor 1 from HTS gave a pharmacophore that eventually turned into potential clinical candidates 17 and 19. During development, a number of issues were successfully addressed, such as metabolic stability, plasma stability, GSH adduct formation, and aniline mutagenicity. Thus, careful modification of the molecule, such as conversion of the 1,4-dihydropyridinone to the 1,2-dihydropyridinone system, proper substitution at C-5″, and in some cases addition of fluorine atoms to the aniline ring allowed for the identification of a novel class of potent P2X7 inhibitors suitable for evaluating the role of P2X7 in inflammatory, immune, neurologic, or musculoskeletal disorders.

Pilot-plant preparation of 3,4-dihydropyridin-2-one derivatives, the core structures ofP2X7 receptor antagonists

The pilot-plant syntheses of 3 and 4, the core structures of a series of P2X7 antagonists are described. The sole stereogenic center in the dihydropyridinone ring was generated by catalytic desymmetrization. Selective formylation, followed by a tandem imination/lactamization sequence, produced the 3,4-dihydropyridin-2-one ring. The compounds 3 and 4 were produced at multikilogram scale in good overall yield (～22% over six steps) and excellent stereochemical purity (97% ee for 3, 100% ee for 4).