HRID1530597

反应详情

EQUATION

反应方程式

HRID 1530597 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-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-9-(1-isopropylpiperidine-4-sulfinyl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene 206 (35 mg, 0.0731 mmol) in DCM (6 mL) was added TFA (17 μL, 0.306 mmol) followed by a slow addition of a solution of m-CPBA (16 mg, 0.0951 mmol) in DCM (1 mL) and the resulting mixture was stirred for 2 h at 0° C. Volatiles were removed under reduced pressure and the resulting residue was purified by column chromatography (C18, gradient 10-40% 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 208 as a white solid (24 mg, 66%). LCMS: RT 2.68 min [M+H]+ 499.1. 1H NMR (DMSO, 400 MHz): δ 8.87 (1H, d, J=2.40 Hz), 7.97 (1H, s), 7.71 (1H, dd, J=10.93, 2.38 Hz), 7.30 (1H, d, J=8.63 Hz), 5.70-5.58 (1H, m), 4.68-4.56 (4H, m), 3.20-3.10 (1H, m), 2.84-2.77 (2H, m), 2.68-2.59 (1H, m), 2.27 (3H, s), 2.09 (2H, bt, J=11.46 Hz), 1.91 (2H, bd, J=12.10 Hz), 1.54-1.34 (8H, m), 0.89 (6H, d, J=6.55 Hz)

WORKUP

后处理

  1. customVolatiles were removed under reduced pressure
  2. customthe resulting residue was purified by column chromatography (C18, gradient 10-40% MeOH in 0.5% TFA/H2O)
  3. washThe cartridge was washed with MeOH
  4. washthe product eluted with 0.5M NH3 in MeOH affording 208 as a white solid (24 mg, 66%)