Triethylamine → 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]-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxamide

Participants

Reaction Steps

Triethylamine (32.2 μL, 0.23 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 (32 mg, 0.077 mmol) and 4-nitrophenyl chloroformate (15 mg, 0.077 mmol) in tetrahydrofuran (1 mL) at 0° C. After 15 min, a solution of the hydrochloride salt of 2,8-diazaspiro[4.5]decan-1-one (15 mg, 0.077 mmol) in dichloromethane (1 mL) and triethylamine (43 μL, 0.31 mmol) were added and the mixture allowed to warm to ambient temperature. After 72 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→87% dichloromethane/methanol) gave the title compound (13 mg). MS 526.2204 (M+1).

Provenance & Evidence