1-Hydroxybenzotriazole → 1-[4-(2-Bromo-benzoyl)-piperazine-1-carbonyl]-cyclopropanecarboxylic acid biphenyl-4-ylamide

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Reaction Steps

DIPEA (140 mg, 1.1 mmol) was added to a stirred solution of N-biphenyl-4-yl-N-methyl-malonamic acid (100 mg, 0.37 mmol) in DMF (2.0 mL) followed by HOBt (60 mg, 0.44 mmol) and EDCI.HCl (85 mg, 0.44 mmol). After 2 minutes of stirring, (2-bromo-phenyl)-piperazin-1-yl-methanone hydrochloride (136 mg, 0.44 mmol) was added and stirring was continued at ambient temperature overnight. The reaction mixture was diluted with water, extracted with ethyl acetate, washed with brine and concentrated under reduced pressure to get the residue. Purification by column chromatography, (using silica gel 60-120, 100% EtOAc as eluent) to afford 14.8 mg (12.95%) of 1-[4-(2-bromo-benzoyl)-piperazine-1-carbonyl]-cyclopropanecarboxylic acid biphenyl-4-ylamide. LC/MS [M+H]+: 520.12, 89.73%. 1H NMR (300 MHz, CDCl3): δ 7.7-7.3 (m, 2H), 7.3-7.2 (m, 2H), 4.0-3.6 (m, 5H), 3.58-3.4 (m, 5H), 3.4-3.2 (m, 3H).

Provenance & Evidence