反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
产物
AUXILIARIES
试剂、催化剂与溶剂
CONDITIONS
反应条件
- 温度
- 0 °C
PROCEDURE
实验过程
To an ice-cooled solution of 8-fluoro-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-9-(1-isopropylpiperidin-4-ylsulfanyl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene 209 (194 mg, 0.40 mmol) in DCM (15 mL) was added TFA (93 μL, 1.20 mmol) followed by a solution of m-CPBA (76 mg, 0.440 mmol) in DCM (2 mL). The resulting mixture was stirred for 15 min at 0° C. then volatiles were removed under reduced pressure. The crude material was purified by column chromatography (C18, gradient 20-45% MeOH in 0.5% TFA/H2O) and then loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH and the product eluted with 0.5M NH3 in MeOH affording 210 as a white solid (167 mg, 83%). LCMS: RT 2.61 min [M+H]+ 501.1. 1H NMR (DMSO, 400 MHz): δ 8.71 (1H, d, J=7.99 Hz), 7.93 (1H, s), 7.15 (1H, d, J=10.69 Hz), 5.69-5.57 (1H, m), 4.66-4.51 (4H, m), 2.89-2.76 (3H, m), 2.72-2.60 (1H, m), 2.26 (3H, s), 2.20-2.06 (2H, m), 1.94-1.85 (1H, bd, J=12.30 Hz), 1.59-1.40 (9H, m), 0.91 (6H, d, J=6.53 Hz)
WORKUP
后处理
- customwere removed under reduced pressure
- customThe crude material was purified by column chromatography (C18, gradient 20-45% MeOH in 0.5% TFA/H2O)
- washThe cartridge was washed with MeOH
- washthe product eluted with 0.5M NH3 in MeOH affording 210 as a white solid (167 mg, 83%)