Trifluoroacetic acid → HCID 89761393, compound

Participants

Reaction Steps

To a solution of 4-(2-cyano-4-(trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-3-methyl-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (790 mg, 1.31 mmol) in dichloromethane (20 mL) was added TFA (2.0 mL, Spectrochem) at 0° C. and the mixture was allowed to stir at room temperature for 16 h. The reaction mixture was concentrated under reduced pressure to get the crude material which was basified (pH˜9) with saturated aqueous NaHCO3 solution. The aqueous layer was extracted with dichloromethane (2×100 mL). The combined organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to get the crude material which was purified by column chromatography (silica gel 100-200 mesh, elution 0-5% methanol in dichloromethane) to obtain 4-(2-cyano-4-(trifluoromethyl)phenyl)-3-methyl-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (530 mg, 84%) as off white solid. 1H NMR (400 MHz, DMSO) δ 12.66 (s, 1H), 8.44 (s, 1H), 8.08 (d, J=7.5 Hz, 1H), 7.67 (d, J=8.4 Hz, 1H), 7.27-7.22 (m, 2H), 7.19 (d, J=8.5 Hz, 1H), 6.82 (d, J=4.5 Hz, 1H), 6.64 (d, J=8.5 Hz, 1H), 4.28-4.03 (m, 3H), 1.20 (d, J=6.5 Hz, 3H); MS (ESI, positive ion) m/z 481.1 (M+H).

Provenance & Evidence