HRID505555

反应详情

EQUATION

反应方程式

HRID 505555 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

2,5-dichloro-3-{[5-chloro-1-(1H-pyrazolo[3,4-b]pyridin-3-ylmethyl)-1H-1,2,3-benzotriazol-4-yl]oxy}benzonitrile (283 mg, 0.601 mmol) was dissolved in dry THF (30 mL), cooled to 0° C., and LAH solution (1.20 mL, 1.20 mmol) in THF (1.2 mL) was added. The reaction mixture was allowed to warm to room temperature, and after 2 hours the mixture was cooled to 0° C. and quenched with EtOAc (50 mL). To this mixture was added saturated aqueous Na2SO4 (3 mL), followed 5 minutes later by the addition of water (5 mL). This mixture was stirred for 5 minutes after which excess solid Na2SO4 was added. The mixture was then filtered and solvent removed under reduced pressure. The resulting residue was purified by reverse phase chromatography eluting with 5-95% MeCN/H2O+0.1% TFA to yield the title compound. 1H NMR (DMSO-d6) δ 8.53 (d, J=4.5 Hz, 1H), 8.12 (d, J=8.0 Hz, 1H), 7.98 (s, 2H), 7.89 (d, J=9.0 Hz, 1H), 7.79 (d, J=9.0 Hz, 1H), 7.48 (s, 1H), 7.20 (dd, J=8.0 Hz, J=4.5 Hz, 1H), 6.91 (s, 1H), 6.38 (s, 2H), 4.21 (s, 2H). HRMS (M+1)=476.0363.

WORKUP

后处理

  1. temperatureto warm to room temperature
  2. temperatureafter 2 hours the mixture was cooled to 0° C.
  3. customquenched with EtOAc (50 mL)
  4. additionTo this mixture was added saturated aqueous Na2SO4 (3 mL)
  5. additionfollowed 5 minutes later by the addition of water (5 mL)
  6. additionwas added
  7. filtrationThe mixture was then filtered
  8. customsolvent removed under reduced pressure
  9. customThe resulting residue was purified by reverse phase chromatography
  10. washeluting with 5-95% MeCN/H2O+0.1% TFA