huagongshe.com
HRID470189

反应详情

EQUATION

反应方程式

HRID 470189 的结构方程式

REACTANTS

反应物

2
结构：C[C@H]1C[C@@H](n2cnc3c(F)cnc(F)c32)[C@@H]2OC(C)(C)O[C@@H]21
HCID58329280

未命名化合物

结构：C[C@H]1C[C@@H](n2cnc3c(F)ncc(F)c32)[C@@H]2OC(C)(C)O[C@@H]21
HCID58329296

未命名化合物

PRODUCTS

生成物

2
结构：C[C@H]1C[C@@H](n2cnc3c(F)cnc(N)c32)[C@@H]2OC(C)(C)O[C@@H]21
HCID67250187

未命名化合物

结构：C[C@H]1C[C@@H](n2cnc3c(N)ncc(F)c32)[C@@H]2OC(C)(C)O[C@@H]21
HCID67250545

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

1
结构：N
溶剂HCID222

Ammonia gas

H3N

CONDITIONS

反应条件

温度
100 °C

PROCEDURE

实验过程

Liquid ammonia (150 mL) was added to a mixture of 4,7-difluoro-1-((3aS,4R,6S,6aR)-2,2,6-trimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-1H-imidazo[4,5-c]pyridine (6-3) (180 mg, 0.6 mmol, 1 equiv) and 4,7-difluoro-3-((3aS,4R,6S,6aR)-2,2,6-trimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-3H-imidazo[4,5-c]pyridine (6-4) (180 mg, 0.6 mmol, 1 equiv). The resulting solution was heated in a high pressure vessel to 100° C. for 2 days. The mixture was then concentrated and purified by flash chromatography (12 g SiO2; 20-100% EtOAc in hexanes and then 100% ethanol to elute 6-3) to yield 7-fluoro-1-((3aS,4R,6S,6aR)-2,2,6-trimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-1H-imidazo[4,5-c]pyridin-4-amine (6-5) as a tan solid and 7-fluoro-3-((3aS,4R,6S,6aR)-2,2,6-trimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-3H-imidazo[4,5-c]pyridin-4-amine (6-6) as a tan solid. LRMS m/z (M+H) 306.9 found, 307.1 required.

WORKUP

后处理

  1. concentrationThe mixture was then concentrated
  2. custompurified by flash chromatography (12 g SiO2
  3. wash20-100% EtOAc in hexanes and then 100% ethanol to elute 6-3)