Trifluoroacetic acid → HCID 89761907, compound

Participants

Reaction Steps

Dissolved 4-(4-cyano-2-methoxyphenyl)-N-(4-methoxybenzyl)-3-oxo-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (133 mg, 0.236 mmol) in 500 μl of DCM in a 10 mL rbf (wrapped with aluminum foil to exclude light) and added trifloroacetic acid (500 μl, 5.91 mmol). The solution was maintained at rt for 30 min until reaction was complete by LCMS. The reaction mixture was concentrated via rotary evaporation then purified using reverse-phase HPLC with a Waters-Xbridge C18, 19×100 mm, 10 μm column with a gradient 5-95% acetonitrile and water with 0.1% NHOH to give 4-(4-cyano-2-methoxyphenyl)-3-oxo-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (23 mg, 0.052 mmol, 22% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 3.78 (s, 3 H) 4.89 (s, 2 H) 6.39 (d, J=8.48 Hz, 1 H) 6.80 (d, J=4.47 Hz, 1 H) 7.23 (d, J=4.47 Hz, 1 H) 7.28-7.35 (m, 1 H) 7.35-7.49 (m, 1 H) 7.53-7.66 (m, 2 H) 7.80 (s, 1 H). m/z ESI 441.0 (M−H)−.

Provenance & Evidence