Trifluoroacetic acid → HCID 89761701, compound

Participants

Reaction Steps

To a solution of N-(4-methoxybenzyl)-4-(2-(pyrimidin-5-yl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (250 mg, 0.437 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 (8 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 (69.61% by LCMS) that was purified by prep purification to obtain 4-(2-(pyrimidin-5-yl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (60 mg, 30.4%) as white solid. 1H NMR (400 MHz, DMSO) δ 12.51 (s, 1H), 9.06 (s, 1H), 8.83 (s, 2H), 7.61 (td, J=6.9, 2.0 Hz, 2H), 7.58-7.48 (m, 2H), 7.21 (d, J=4.7 Hz, 1H), 7.01 (td, J=4.8, 4.2, 1.8 Hz, 2H), 6.77 (d, J=4.7 Hz, 1H), 6.21 (d, J=9.0 Hz, 1H), 4.30 (dt, J=11.1, 3.2 Hz, 1H), 4.03 (ddd, J=10.9, 8.6, 2.7 Hz, 1H), 3.76 (ddd, J=11.3, 8.3, 3.0 Hz, 1H), 3.44 (dt, J=12.3, 3.1 Hz, 1H); MS (ESI, positive ion) m/z: 452.1 (M+1).

Provenance & Evidence