Diisopropylethylamine → HCID 178509914, compound

Participants

Reaction Steps

DMF (5 mL) was added to a mixture of 3-{[5-(aminomethyl)-2-chlorophenyl]oxy}-5-chlorobenzonitrile hydrochloride (0.115 g, 0.349 mmol), 4-bromo-1H-imidazole-5-carboxylic acid (0.070 g, 0.366 mmol) and HATU (0.159 g, 0.419 mmol). The mixture was stirred for 5 min then DIPEA (0.122 ml, 0.698 mmol) was added and the yellow solution was stirred at RT under an atmosphere of nitrogen for 2 h. Saturated aqueous NaHCO3 solution (30 mL) and ethyl acetate (75 mL) were added. The organic layer was separated, washed with saturated aqueous NaHCO3 solution (2×50 mL), water (50 mL), brine (50 mL), dried over MgSO4, filtered and concentrated. The crude material was purified by Reverse Phase HPLC (MeCN/water+0.1% TFA) to give the title compound (0.026 g, 16%) as a white solid. 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.74 (br. s., 1H), 7.49-7.56 (m, 2H), 7.30 (d, 1H), 7.16-7.24 (m, 3H), 4.57 (br. s., 2H). LCMS m/z 467.1 (M+H).

Provenance & Evidence