1-Hydroxybenzotriazole → N-[1-[[(4R)-5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-yl]carbamoyl]cyclopropyl]-4-ethoxy-benzamide

Participants

Reaction Steps

Combine (4R)-5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-amine (0.50 g, 2.51 mmol), 1-[(4-ethoxybenzoyl)amino]cyclopropanecarboxylic acid (0.75 mg, 3.01 mmol), 1-hydroxybenzotriazole (407 mg, 3.01 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (577 mg, 3.01 mmol) in tetrahydrofuran (40 mL). Add diisopropylethylamine (0.53 mL, 3.01 mmol) and stir the reaction for approximately 16 hours at ambient temperature under nitrogen. Dilute the reaction with ethyl acetate, wash with saturated sodium bicarbonate and brine, dry over sodium sulfate, and concentrate the organic layer under reduced pressure. Purify the residue by flash chromatography (25% EtOAc/hexanes to 100% EtOAc) to give the title compound (860 mg, 80%): MS (m/z): 431 (M+1).

Provenance & Evidence