Ethylamine hydrochloride → HCID 54575465, compound

Participants

Reaction Steps

To a solution of 4-({5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazol-4-yl}methoxy)benzoic acid (0.48 g, 1.05 mmol), ethylamine hydrochloride (0.09 g, 1.05 mmol) and DIPEA (0.55 ml, 3.15 mmol) in 9 mL of DMF was added BOP (0.56 g, 1.26 mmol). It was stirred at room temperature for 2 h. Water was added and extracted with EA. The organic layers were combined and washed with 3M LiCl (3×), dried over Na2SO4, filtered and concentrated. The reaction was purified by flash chromatography (silica, 30-70% EtOAc/hexanes) to give 4-({5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazol-4-yl}methoxy)-N-ethylbenzamide: 1H NMR (400 MHz, CDCl3) δ 8.35 (d, J=2.5 Hz, 1H), 8.08 (m, 2H), 7.66 (d, J=8.7 Hz, 2H), 7.48 (dd, J=8.4, 2.6 Hz, 1H), 7.15 (m, 2H), 6.96 (m, 3H), 5.95 (s, 1H), 5.15 (s, 2H), 3.45 (m, 2H), 1,22 (t, J=7.3 Hz, 3H); HRMS exact mass calc for C24H19ClFN3O3S [M+H]+: 484.0892; observed: 484.0900.

Provenance & Evidence