HRID1530578

反应详情

EQUATION

反应方程式

HRID 1530578 的结构方程式

AUXILIARIES

试剂、催化剂与溶剂

1

CONDITIONS

反应条件

温度
0 °C

PROCEDURE

实验过程

To an ice-cooled solution of 2-{4-[2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-9-ylsulfanyl]piperidin-1-yl}-2-methylpropan-1-ol from Example 1 (229 mg, 0.474 mmol) in DCM (10 mL) was added TFA (110 μL, 1.42 mmol) followed by a solution of m-CPBA (82 mg, 0.474 mmol) in DCM (2 mL). The resulting mixture was stirred for 1 h at 0° C. then volatiles were removed under reduced pressure. The crude material was purified by column chromatography (C18, gradient 10-35% MeOH in 0.5% TFA/H2O) and then loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH and the product was eluted with 0.5M NH3 in MeOH affording 186 as a white solid (177 mg, 75%). LCMS: RT 2.45 min [M+H]+ 499.2. 1H NMR (DMSO, 400 MHz): δ 8.59 (1H, d, J=2.26 Hz), 7.97 (1H, s), 7.93 (1H, s), 7.53 (1H, dd, J=8.53, 2.28 Hz), 7.25 (1H, d, J=8.53 Hz), 5.80-5.67 (1H, m), 4.61-4.43 (4H, m), 4.22-4.16 (1H, m), 3.21 (2H, d, J=4.59 Hz), 3.06-2.96 (2H, m), 2.73-2.63 (1H, m), 2.17-2.05 (2H, m), 1.77 (1H, bd, J=12.25 Hz), 1.59 (1H, bd, J=12.59 Hz), 1.52-1.34 (8H, m), 0.88 (6H, s)

WORKUP

后处理

  1. customwere removed under reduced pressure
  2. customThe crude material was purified by column chromatography (C18, gradient 10-35% MeOH in 0.5% TFA/H2O)
  3. washThe cartridge was washed with MeOH
  4. washthe product was eluted with 0.5M NH3 in MeOH affording 186 as a white solid (177 mg, 75%)