1-Hydroxybenzotriazole → HCID 56296296, compound

Participants

Reaction Conditions

Reaction Steps

HOBt (44.6 mg, 0.33 mmol) and DIPEA (136.7 mg, 1.06 mmol) were added to a stirred solution of 5-phenyl-isoxazole-3-carboxylic acid (50 mg, 0.27 mmol) in DMF (1.0 mL). The reaction mixture was then cooled to 10° C. and EDCI.HCl (63.3 mg, 0.33 mmol) was added, followed by the addition 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone (as TFA salt) (113.5 mg, 0.27 mmol). Then resulting mixture was stirred at room temperature overnight. The reaction mixture was then diluted with water and the product extracted with ethyl acetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated. The crude product thus obtained was purified by column chromatography using neutral alumina as stationary phase and 100% ethyl acetate as the eluent to afford 5-phenyl-isoxazole-3-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide as a solid in 20.3% yield. LC-MS purity: 98.075%, 1H NMR (DMSO-D6): δ 8.6 (s, 1H), 7.9 (m, 2H), 7.7 (m, 2H), 7.65 (m, 1H), 7.5 (m, 3H), 7.4 (s, 1H), 4.1 (m, 2H), 3.6 (m, 4H), 3.4 (m, 2H), 3.1 (m, 2H).

Provenance & Evidence