Hydrochloric Acid → HCID 66621163, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-oxo-2-(2-(pyridin-3-yl)benzo[d]oxazol-4-yl)acetic acid (135 mg, 0.56 mmol) in DMF (15 mL) was added HOBt (148 mg, 1.1 mmol), NH4Cl (54 mg, 1.0 mmol), DIPEA (387 mg, 3.0 mmol) and EDCI (211 mg, 1.1 mmol). The mixture was stirred at 25° C. for 10 hr. To the resulting mixture, water (10 mL) and 1N aqueous hydrochloric acid was added to pH=3, then extracted with ethyl acetate (100 mL×4). The organic phase was washed with saturated sodium bicarbonate solution and brine, concentrated, and dried in vacuum. The crude product was purified by preparative HPLC to obtain 2-(pyridin-3-yl)benzo[d]oxazole-4-carboxamide as a solid (25 mg, yield 18%). 1H-NMR (400 MHz, DMSO-d6) δ 7.52-7.56 (t, J=8 Hz, 1H), 7.88-7.95 (m, 3H), 8.03-8.05 (d, J=8 Hz, 1H), 8.21-8.22 (d, J=4 Hz, 2H), 8.86 (d, J=4 Hz, 2H); LC-MS (ESI) m/z 240 [M+1]+.

Provenance & Evidence