Trifluoroacetic acid → HCID 89761679, compound

Participants

Reaction Steps

To a solution of N-(4-methoxybenzyl)-4-(2-(methylsulfonyl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (200 mg, 0.350 mmol) in DCM (5 mL) was added TFA (2 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 (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 (71% by LCMS) that was purified by prep purification to obtain 4-(2-(methylsulfonyl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (28 mg, 17.8%) as white solid. 1H NMR (400 MHz, DMSO) δ 12.51 (s, 1H), 8.07 (d, J=7.8 Hz, 1H), 7.85 (t, J=7.7 Hz, 1H), 7.77-7.54 (m, 2H), 7.19 (dd, J=15.2, 3.4 Hz, 2H), 7.08 (dd, J=8.7, 2.1 Hz, 1H), 6.77 (d, J=4.7 Hz, 1H), 6.21 (d, J=8.5 Hz, 1H), 4.42 (dt, J=10.9, 3.3 Hz, 1H), 4.34 (dd, J=10.9, 5.4 Hz, 1H), 3.61 (t, J=3.9 Hz, 2H), 3.18 (s, 3H); MS (ESI, positive ion) m/z: 452.0 (M+1).

Provenance & Evidence