Triethylamine → HCID 11721059, compound

Participants

Reaction Steps

Triethylamine (33.0 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 (33.0 mg, 0.079 mmol) and 4-nitrophenyl chloroformate (16.0 mg, 0.079 mmol) in tetrahydrofuran (1 mL) at 0° C. After 15 min, a solution of 6-methyl-4-piperidin-4-ylpyridazin-3(2H)-one (15.0 mg, 0.079 mmol) in dichloromethane (1 mL) and triethylamine (22 μL, 0.16 mmol) were added and the mixture allowed to warm to ambient temperature. After 4 h, saturated aqueous sodium carbonate was added and the mixture was extracted with ethyl acetate (3×). 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 the title compound (22 mg). MS 565.2306 (M+1).

Provenance & Evidence