反应详情

温度

10 °C

HOBt (72 mg, 0.53 mmol) and DMAP (81 mg, 0.66 mmol) were added to a stirred solution of 3-oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionic acid (150 mg, 0.44 mmol) in DMF (2 mL). The reaction mixture was cooled to 10° C. and EDCI.HCl (102 mg, 0.53 mmol) followed by 4-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenylamine (77 mg, 0.44 mmol) were added. The reaction mixture was stirred at room temperature overnight then diluted with water and the product extracted with ethyl acetate. The organics were washed with brine solution, dried over Na2SO4 and concentrated. The residue was purified by column chromatography using basic alumina (80% ethyl acetate in hexane) to afford 40 mg (20%) of N-[4-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenyl]-3-oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionamide. LCMS: 502.17 (M+1)+, 94.56%, 1H NMR: (DMSO-d6): δ 10.5 (d, 1H), 7.92 (m, 2H), 7.8 (m, 4H), 7.68 (t, 1H), 7.56 (m, 1H), 3.68 (m, 7H), 3.44 (m, 2H), 3.18 (m, 1H), 3.08 (m, 1H), 2.58 (s, 3H).

1. additionwere added
2. extractionthe product extracted with ethyl acetate
3. washThe organics were washed with brine solution
4. dry with materialdried over Na2SO4
5. concentrationconcentrated
6. customThe residue was purified by column chromatography