Dimethylformamide → HCID 44231209, compound

Participants

Reaction Conditions

Reaction Steps

HOBt (153 mg, 1.13 mmol) and DMAP (172 mg, 1.4 mmol) were added to a stirred solution of 3-oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionic acid (325 mg, 9.45 mmol) in DMF (2 mL). The reaction mixture was cooled to 10° C. and EDCI.HCl (217 mg, 1.13 mmol) followed by 4-[1,2,4]oxadiazol-3-yl-phenylamine-2-yl-amine (152 mg, 9.4 mmol) were added. The reaction mixture was stirred at the 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 evaporated. The residue was washed with ether and dried to afford 220 mg (48%) of N-(4-[1,2,4]oxadiazol-3-yl-phenyl)-3-oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionamide. LCMS: 488.15 (M+1)+, 96.97%. 1H NMR: (CDCl3): δ 10.0 (d, 1H), 8.74 (s, 1H), 8.08 (d, 2H), 7.7 (m, 3H), 7.6 (m, 2H), 7.34 (d, 1H), 4.02 (m, 2H), 3.7 (m, 3H), 3.5 (m, 4H), 3.26 (m, 2H).

Provenance & Evidence