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]-4-(2,4-dioxoimidazolidin-1-yl)piperidine-1-carboxamide

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Reaction Steps

Triethylamine (16 μL, 0.11 mmol) was added to a solution 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 (38 mg, 0.11 mmol) and 4-nitrophenyl chloroformate (23 mg, 0.11 mmol) in tetrahydrofuran (2 mL) at 0° C. After 1 h, 1-piperidin-4-ylimidazolidine-2,4-dione (21 mg, 0.11 mmol) and triethylamine (47 μL, 0.33 mmol) were added and the mixture allowed to warm to ambient temperature. After 1 h, saturated aqueous sodium carbonate was added and the mixture was extracted with dichloromethane. The organic layer was washed with saturated aqueous sodium bicarbonate (3×), saturated brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography [100% dichloromethane→93% dichloromethane/methanol] gave the title compound (36 mg). MS 555.2126 (M+1).

Provenance & Evidence