Pyridine → N-(2-carbamoylphenyl)-1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxamide

Participants

Reaction Steps

To a suspension of 1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acid (Intermediate J, 100 mg, 0.41 mmol) in CH2Cl2 (1.5 mL) is added 1-chloro-N,N,2-trimethylpropenylamine (0.20 mL, 1.43 mmol). The reaction mixture is stirred for 5 h. 2-Aminobenzamide (200 mg, 1.47 mmol) and pyridine (0.12 mL, 1.48 mmol) are added and the reaction mixture is stirred for another 16 h at room temperature. Water (55 mL) is added and the resulting white solid is collected by filtration and purified by flash column chromatography using methanol in CH2Cl2 to afford the title compound (40 mg, 27%). LCMS (ESMS): m/z 363.61 (M+H+).

Provenance & Evidence