反应详情

温度

90 °C

2-(4-(4-Bromo-1-methyl-1H-pyrazole-3-carbonyl)piperazin-1-yl)-1-(4-fluorophenyl)ethanone (100 mg, 0.24 mmol) and methoxylamine hydrochloride (25 mg, 0.31 mmol) were taken up in ethanol (10 mL) in a round-bottom flask and heated to reflux at 90° C. for 21 h. The solvent was removed under reduced pressure and saturated aqueous NaHCO3 (1.5 mL) was added. The mixture was extracted three times with DCM and the organic phase was dried over sodium sulfate, filtered, and concentrated. The crude product was purified by preparative TLC plate (Rf=0.44, 60% EtOAc/Hexane, UV 254 nm) and dried to afford the title compound (25 mg) as a free base. 1H NMR (Acetonitrile-d3, 400 MHz) δ 2.42-2.48 (m, 2H), 2.48-2.54 (m, 2H), 3.35-3.42 (m, 2H), 3.37 (s, 2H), 3.57-3.63 (m, 2H), 3.80 (s, 3H), 3.84 (s, 3H), 7.14 (t, J=8.84 Hz, 2H), 7.60 (dd, J=5.31, 8.84 Hz, 2H), 7.61 (s, 1H). Exact mass calculated for C18H21BrFN5O2: 437.1. Found: LCMS m/z (%)=438.3 (M+H+79Br, 100%), 440.3 (M+H+81Br, 97%).

1. temperatureheated
2. customThe solvent was removed under reduced pressure and saturated aqueous NaHCO3 (1.5 mL)
3. additionwas added
4. extractionThe mixture was extracted three times with DCM
5. dry with materialthe organic phase was dried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customThe crude product was purified by preparative TLC plate (Rf=0.44, 60% EtOAc/Hexane, UV 254 nm)
9. customdried