1,2-Dichloroethane → HCID 178509909, compound

Participants

Reaction Steps

EDC (0.029 g, 0.152 mmol) and HOBT (0.021 g, 0.152 mmol) were added to a solution of 3-{[3-(aminomethyl)-6-bromo-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.049 g, 0.138 mmol) and 2-(bis{[(1,1-dimethylethyl)oxy]carbonyl}amino)-4-chloro-1H-imidazole-5-carboxylic acid (0.050 g, 0.138 mmol) in DMF (2 mL). The mixture was stirred at RT for 1 hr. The reaction mixture was extracted with EtOAc and saturated sodium bicarbonate. The organic layer was dried over sodium sulfate and concentrated to an oil. Dichloromethane (2 mL) and trifluoroacetic acid (0.5 mL, 6.49 mmol) were added and the mixture was stirred at RT overnight. The solvent was evaporated and the residue was purified by reverse phase HPLC (acetonitrile:water with 0.1% formic acid) to give the title compound (0.0103 g, 18%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.05 (br. s., 1H), 7.75-7.85 (m, 2H), 7.61 (d, 1H), 7.49 (s, 1H), 7.43 (m, 1H), 7.21-7.32 (m, 1H), 5.82 (br. s., 2H), 4.47 (d, 2H). LCMS: m/z 499 (M+1).

Provenance & Evidence