反应详情

温度

25 °C

To a solution of 4-amino-3-hydroxy-N-(4-methoxybenzyl)-N-(thiazol-2-yl)benzenesulfonamide (INTERMEDIATE AD) (2.0 g, 5.12 mmol) in DMF (15 mL) was added K2CO3 (2.1 g, 15.3 mmol, Quaigens). To the above suspension was added 2-chloropropanoyl chloride (0.780 g, 6.15 mmol) at 0° C. and reaction mixture was stirred at 25° C. for 30 min, then heated 60° C. for 3 h. The reaction mixture was cooled to 25° C. The organic compound was extracted with EtOAc, washed with water, dried over sodium sulfate and concentrated. The resulting residue was purified by silica gel column chromatography using a gradient of 0-50% EtOAc in hexanes as the eluent to afford 1.45 g of N-(4-methoxybenzyl)-2-methyl-3-oxo-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide as off white solid in 63.6% yield. 1H-NMR (400 MHz, DMSO): δ 7.45-7.46 (m, 2H), 7.40-7.44 (m, 1H), 7.23-7.26 (m, 3H), 7.02 (d, J=8.4 Hz, 1H), 6.85 (d, J=8.8 Hz, 2H), 5.19 (s, 2H), 3.70 (s, 3H), 1.44 (t, J=6.8 Hz, 3H); m/z (ESI, positive ion) 445.9 (M+H).

1. customreaction mixture
2. temperatureheated 60° C. for 3 h
3. temperatureThe reaction mixture was cooled to 25° C
4. extractionThe organic compound was extracted with EtOAc
5. washwashed with water
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated
8. customThe resulting residue was purified by silica gel column chromatography