1-Hydroxybenzotriazole → 3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-N-[4-(2-oxo-2H-pyridin-1-yl)-phenyl]-propionamide

Participants

Reaction Conditions

Reaction Steps

HOBt (75 mg, 0.55 mmol) and DIPEA (213 mg, 1.65 mmol) were added to a stirred solution of N-[4-(2-oxo-2H-pyridin-1-yl)-phenyl]-malonamic acid (150 mg, 0.55 mmol) in DMF (2.0 mL). The reaction mixture was cooled to 0° C. and EDCI.HCl (126 mg, 0.66 mmol) followed by (2-bromo-phenyl)-piperazin-1-yl-methanone hydrochloride (185 mg, 0.6 mmol) were added. The reaction mixture was stirred at room temperature overnight then diluted with water. The resulting precipitate was recrystallized from ethyl acetate:hexane (1:1) to afford 180 mg (21%) of 3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-N-[4-(2-oxo-2H-pyridin-1-yl)-phenyl]-propionamide. LCMS: 524.09 (M+1)+9.7%, 1H NMR: (DMSO-d6): δ 7.7-7.2 (m, 8H), 6.5 (m, 1H), 6.3 (m, 1H), 3.8-3.6 (m, 5H), 3.6-3.34 (m, 3H), 3.2 (m, 2H).

Provenance & Evidence