1369959-23-8

Basic information

• Product Name: (R)-tertbutyl-7-(3,4-dichlorophenyl)-6-((S)-2-(4-fluorophenyl)pyrrolidine-1-carbonyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidine-4(7H)-carboxylate
• Synonyms: (R)-tertbutyl-7-(3,4-dichlorophenyl)-6-((S)-2-(4-fluorophenyl)pyrrolidine-1-carbonyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidine-4(7H)-carboxylate
• CAS NO: 1369959-23-8
• Molecular Weight: 585.506
• Mol File: 1369959-23-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (R)-tertbutyl-7-(3,4-dichlorophenyl)-6-((S)-2-(4-fluorophenyl)pyrrolidine-1-carbonyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidine-4(7H)-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-tertbutyl-7-(3,4-dichlorophenyl)-6-((S)-2-(4-fluorophenyl)pyrrolidine-1-carbonyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidine-4(7H)-carboxylate(1369959-23-8)
• EPA Substance Registry System: (R)-tertbutyl-7-(3,4-dichlorophenyl)-6-((S)-2-(4-fluorophenyl)pyrrolidine-1-carbonyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidine-4(7H)-carboxylate(1369959-23-8)

Safety Data

• Hazardous Substances Data: 1369959-23-8(Hazardous Substances Data)

Upstream product

• 6287-38-3 3,4-dichlorobenzaldehyde 
• 1369959-20-5 4-tert-butyl-6-methyl-7-(3,4-dichlorophenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidine-4,6(7H)-dicarboxylate 
• 1369959-19-2 methyl 7-(3,4-dichlorophenyl)-2,5-dimethyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxylate 
• 298690-90-1 (S)-2-(4-fluorophenyl)pyrrolidine 
• 1369959-01-2 (R)-4-(tert-butoxycarbonyl)-7-(3,4-dichlorophenyl)-2,5-dimethyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxylic acid 

Downstream Products

• 1369958-91-7 ((R)-7-(3,4-dichlorophenyl)-2,5-dimethyl-4,7-dihydropyrazolo-[1,5-a]pyrimidin-6-yl) ((S)-2-(4-fluorophenyl)pyrrolidin-1-yl)methanone 

Relevant articles and documents

Discovery of ((S)-5-(methoxymethyl)-7-(1-methyl-1 H -indol-2-yl)-2- (trifluoromethyl)-4,7-dihydropyrazolo[1,5- a ]pyrimidin-6-yl)((S)-2-(3- methylisoxazol-5-yl)pyrrolidin-1-yl)methanone as a potent and selective I Kur inhibitor

Previously disclosed dihydropyrazolopyrimidines are potent and selective blockers of IKur current. A potential liability with this chemotype is the formation of a reactive metabolite which demonstrated covalent binding to protein in vitro. When substituted at the 2 or 3 position, this template yielded potent IKur inhibitors, with selectivity over hERG which did not form reactive metabolites. Subsequent optimization for potency and PK properties lead to the discovery of ((S)-5-(methoxymethyl)-7-(1-methyl-1H-indol- 2-yl)-2-(trifluoromethyl)-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)((S) -2-(3-methylisoxazol-5-yl)pyrrolidin-1-yl)methanone (13j), with an acceptable PK profile in preclinical species and potent efficacy in the preclinical rabbit atrial effective refractory period (AERP) model.