1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-biphenyl-4-yl-3-[4-(2-bromo-benzoyl)-[1,4]diazepan-1-yl]-3-oxo-propionamide

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Reaction Steps

DIPEA (146 mg, 0.2 mL, 1.17 mmol) was added dropwise to N-biphenyl-4-yl-malonamic acid (100 mg, 0.39 mmol) in DMF (2 mL) followed by EDCI (90 mg, 0.47 mmol) and HOBT (63 mg, 0.47 mmol). After 2 minutes, (2-bromo-phenyl)-[1,4]diazepan-1-yl-methanone hydrochloride (150 mg, 0.47 mmol) was added and stirring was continued at room temperature overnight. Cold water was then added and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure to afford 110 mg (54.18% yield) of N-biphenyl-4-yl-3-[4-(2-bromo-benzoyl)-[1,4]diazepan-1-yl]-3-oxo-propionamide. LC/MS [M+H]+: 520.12, 96.67%. 1H NMR (300 MHz, DMSO-d6): δ 10.3-10.2 (m, 1H), 7.8-6.7 (m, 13H), 4.1-3.4 (m, 9H), 3.3-3.0 (m, 2H), 2.0-1.8 (m, 1H), 1.7-1.5 (m, 1H).

Provenance & Evidence