1,2-Dichloroethane → HCID 178436401, compound

Participants

Reaction Steps

A solution of 3-{[3-(aminomethyl)-6-ethyl-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.075 g, 0.246 mmol), 4-chloro-2-methyl-1H-imidazole-5-carboxylic acid (0.040 g, 0.246 mmol), EDC (0.047 g, 0.246 mmol) and HOBT (0.038 g, 0.246 mmol) in DMF (4 ml) was stirred at RT under an atmosphere of nitrogen for 1 h then ethyl acetate (100 mL) and saturated aqueous NaHCO3 solution (100 mL) were added. The organic layer was separated, washed with saturated aqueous NaHCO3 solution (100 mL), water (100 mL), dried over MgSO4, filtered and concentrated. The material was purified by Reverse Phase HPLC (MeCN/water+0.1% TFA). The desired product was washed with saturated NaHCO3 solution and extraced with ethyl acetate. The organic layer was separated, washed with saturated aqueous NaHCO3 solution (50 mL), water (50 mL), dried over MgSO4, filtered and concentrated to give the title compound (0.052 g, 47%) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 11.06 (br. s., 1H), 7.29 (s, 1H), 7.20 (d, 1H), 7.03-7.12 (m, 3H), 6.97 (s, 1H), 4.67 (d, 2H), 2.53 (q, 2H), 2.37 (s, 3H), 1.13 (t, 3H). LCMS m/z 447.05 (M+H).

Provenance & Evidence