Triethylamine → HCID 11498007, compound

Participants

Reaction Steps

Triethylamine (34 μL, 0.24 mmol) was added to a solution of the hydrochloride salt of (6S,9R)-6-(2,3-difluorophenyl)-3-(2,2,2-trifluoroethyl)-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-9-amine (36 mg, 0.081 mmol) and 4-nitrophenyl chloroformate (16 mg, 0.081 mmol) in dichloromethane (1 mL) at 0° C. After 15 min, a solution of a mixture of 6-cyclopropyl-4-piperidin-4-ylpyridazin-3(2H)-one and 4-piperidin-4-yl-6-propylpyridazin-3(2H)-one (18 mg, 0.081 mmol) in dichloromethane (1 mL) and triethylamine (11 μL, 0.08 mmol) were added and the mixture allowed to warm to ambient temperature. After 3 h, saturated aqueous sodium carbonate was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate (3×), saturated brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→90% dichloromethane/methanol) gave 4-(6-cyclopropyl-3-oxo-2,3-dihydropyridazin-4-yl)-N-[(6S,9R)-6-(2,3-difluorophenyl)-3-(2,2,2-trifluoroethyl)-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-9-yl]piperidine-1-carboxamide (11 mg); MS 591.2507 (M+1) and N-[(6S,9R)-6-(2,3-difluorophenyl)-3-(2,2,2-trifluoroethyl)-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-9-yl]-4-(3-oxo-6-propyl-2,3-dihydropyridazin-4-yl)piperidine-1-carboxamide (14 mg); MS 593.2689 (M+1).

Provenance & Evidence