Trifluoroacetic acid → HCID 89761725, compound

Participants

Reaction Steps

To a solution of 4-(2-(cyanomethoxy)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (200 mg, 0.364 mmol) in DCM (30 mL) was added TFA (0.5 mL) at 0° C. The reaction mixture was stirred at ambient temperature for 2 h. After completion, the reaction mixture was quenched with saturated aqueous sodium bicarbonate solution (20 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain the crude product which was purified by prep HPLC purification to obtain 4-(2-(cyanomethoxy)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide as a white solid (39 mg, 25%). MS (ESI, positive ion) m/z; 429.0 (M+1). 1H NMR (400 MHz, DMSO) δ 12.50 (s, 1H), 7.42-7.36 (m, 2H), 7.36-7.30 (m, 1H), 7.23-7.15 (m, 2H), 7.12 (d, J=2.0 Hz, 1H), 7.08 (dd, J=8.5, 2.1 Hz, 1H), 6.77 (d, J=4.5 Hz, 1H), 6.19 (d, J=8.5 Hz, 1H), 5.18 (s, 2H), 4.32 (t, J=4.2 Hz, 2H), 3.64 (t, J=4.2 Hz, 2H).

Provenance & Evidence