4-Chlorobenzoic Acid → HCID 67235365, compound

Participants

Reaction Steps

Combine 1-amino-N-(5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-yl)cyclopentanecarboxamide (158 mg, 509.02 μmoles), 4-chlorobenzoic acid (95.64 mg, 610.83 μmoles), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (117.10 mg, 610.83 μmoles), and 1-hydroxybenzotriazole (82.54 mg, 610.83 μmoles;) in tetrahydrofuran (12 mL). Add diisopropylethylamine (106.53 μL, 610.83 μmoles) and stir the reaction at ambient temperature for approximately 16 hours. Dilute the reaction with EtOAc, wash with dilute sodium bicarbonate and brine, dry over sodium sulfate, and concentrate the organic layer under reduced pressure. Purify the residue by flash chromatography (0-40% of a 5% solution of ammonia/methanol/dichloromethane (2N)/dichloromethane) to give the title compound (101.0 mg, 44%): MS (m/z): 449 (M+1).

Provenance & Evidence