1,1'-Carbonyldiimidazole → N-{(6S,9R)-6-(2,3-Difluorophenyl)-3-[1-(trifluoromethyl)cyclopropyl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-9-yl}-4-(3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamide

Participants

Reaction Conditions

Reaction Steps

1,1′-Carbonyldiimidazole (24.0 mg, 0.15 mmol) was added to a solution of (6S,9R)-6-(2,3-difluorophenyl)-3-[1-(trifluoromethyl)cyclopropyl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-9-amine (28 mg, 0.075 mmol) and in tetrahydrofuran (1.0 mL) at 0° C. After 30 min, additional 1,1′-carbonyldiimidazole (11.0 mg, 0.068 mmol) was added. After 30 min, 3-methyl-1-piperidin-4-yl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (26 mg, 0.113 mmol) was added and the mixture was heated to 60° C. After 1 h, additional 3-methyl-1-piperidin-4-yl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (23 mg, 0.099 mmol) was added. After 1 h, the reaction mixture was concentrated. Purification by reverse phase HPLC (100% water→100% acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (33 mg). MS 631.2566 (M+1).

Provenance & Evidence