Trifluoroacetic acid → HCID 89761866, compound

Participants

Reaction Steps

To a solution of 4-(2-(2-hydroxy-2-methylpropoxy)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (600 mg, 0.585 mmol) in DCM (5 mL) was added TFA (1.4 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 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 purification to obtain 4-(2-(2-hydroxy-2-methylpropoxy)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (120 mg, 26.0%) as a white solid. m/z (ESI) 461.8 (M+H)+. 1H NMR (400 MHz, DMSO) δ 12.50 (s, 1H), 7.38-7.24 (m, 2H), 7.20 (d, J=4.6 Hz, 1H), 7.16-6.95 (m, 4H), 6.76 (d, J=4.3 Hz, 1H), 6.23-6.00 (m, 1H), 4.46 (s, 1H), 4.31 (d, J=3.9 Hz, 2H), 3.61-3.58 (m, 4H), 0.83 (s, 6H).

Provenance & Evidence