Trifluoroacetic acid → HCID 89761548, compound

Participants

Reaction Steps

To a solution of N-(4-methoxybenzyl)-4-(2-(2-methoxyethoxyl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (300 mg, 0.529 mmol) in DCM (6 mL) was added TFA (3 mL) 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 reduced pressure to obtain the crude material (36% by LCMS) that was purified by prep purification to obtain 4-(2-(2-methoxyethoxyl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (38 mg, 16.1%) as white solid. 1H NMR (400 MHz, DMSO) δ 12.49 (s, 1H), 7.38-7.25 (m, 2H), 7.25-7.13 (m, 2H), 7.14-6.95 (m, 3H), 6.75 (d, J=4.6 Hz, 1H), 6.22 (d, J=8.5 Hz, 1H), 4.28 (t, J=4.3 Hz, 2H), 4.07 (dd, J=5.6, 3.5 Hz, 2H), 3.62 (t, J=4.1 Hz, 2H), 3.47 (t, J=4.5 Hz, 2H), 3.10 (s, 3H); MS (ESI, positive ion) m/z: 448.09 (M+1).

Provenance & Evidence