Trifluoroacetic acid → 4-(2-(1,2-dihydroxyethyl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

Participants

Reaction Steps

To a solution of 4-(2-(1,2-dihydroxyethyl)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (300 mg, 0.585 mmol) in DCM (5 mL) was added TFA (0.7 mL, Spectrochem) 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 (10 mL) and extracted with DCM (2×10 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain the crude material which was purified by prep HPLC to obtain 4-(2-(1,2-dihydroxyethyl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (14 mg, 5.9%) as a white solid. m/z (ESI) 434.0 (M+H)+. 1H NMR (400 MHz, DMSO) δ 12.48 (s, 1H), 7.61 (d, J=5.0 Hz, 1H), 7.37 (d, J=4.5 Hz, 2H), 7.23 (t, J=7.7 Hz, 1H), 7.16 (d, J=4.3 Hz, 1H), 7.11 (s, 1H), 7.05 (d, J=8.6 Hz, 1H), 6.71 (d, J=4.2 Hz, 1H), 6.05 (d, J=8.5 Hz, 1H), 5.16 (s, 1H), 4.66 (d, J=25.7 Hz, 2H), 4.34 (q, J=10.8, 10.3 Hz, 2H), 3.77 (t, J=8.3 Hz, 1H), 3.68-3.45 (m, 3H).

Provenance & Evidence