Trifluoroacetic acid → HCID 89761981, compound

Participants

Reaction Steps

In a 25-mL round bottom flask was dissolved 4-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-3-oxo-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide in 4 mL of DCM then treated with TFA (2.384 mL, 30.9 mmol). After 30 min the reaction mixture was concentrated under reduced pressure and purified by MPLC (ISCO) with DCM:MeOH 100:0 to 90:10 to afforded 4-(2-methoxy-4-(trifluoromethyl)phenyl)-3-oxo-N-(thiazol-2-yl)-3,4-dihydro-2H benzo[b][1,4]oxazine-7-sulfonamide (250 mg, 0.515 mmol, 83.0% yield from INTERMEDIate AB2) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.81 (s, 3 H) 4.91 (s, 2 H) 6.41 (d, J=8.41 Hz, 1 H) 6.83 (d, J=4.60 Hz, 1 H) 7.26 (d, J=4.60 Hz, 1 H) 7.34 (dd, J=8.36, 2.01 Hz, 1 H) 7.38 (d, J=1.96 Hz, 1 H) 7.51 (d, J=8.12 Hz, 1 H) 7.55-7.65 (m, 2 H) 12.75 (br. s., 1 H). m/z (ESI) 486.0 (M+H)+.

Provenance & Evidence