(5S,6S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(4-fluoro-phenyl)-3-(2-methanesulfonyl-pyrimidin-4-yl)-6-methyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole | 926660-16-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (5S,6S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(4-fluoro-phenyl)-3-(2-methanesulfonyl-pyrimidin-4-yl)-6-methyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole
• CAS: 926660-16-4
• 化学式: C₃₅H₃₇FN₄O₃SSi
• 分子量: 640.854
• InChiKey: RQTUYMFREQLXOO-QABMSTFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.86
• 重原子数：
  45.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  86.97
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (5S,6S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(4-fluoro-phenyl)-3-(2-methanesulfonyl-pyrimidin-4-yl)-6-methyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole 、 正丙胺 反应 8.0h， 以93%的产率得到{4-[5-(tert-butyldiphenylsilanyloxymethyl)-2-(4-fluorophenyl)-6-methyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl]-pyrimidin-2-yl}-propylamine
  参考文献：
  名称：

  Synthesis of Potent Bicyclic Bisarylimidazole c-Jun N-Terminal Kinase Inhibitors by Catalytic C−H Bond Activation

  摘要：

  The efficient preparation of the privileged bicyclic bisarylimidazole kinase inhibitor scaffold was accomplished using rhodium-catalyzed C-H activation and intramolecular alkylation. The key C-H activation/alkylation step represents one of the first evaluations of diastereocontrol in catalyzed C-H activation/olefin alkylation processes. Several inhibitors of JNK3 were prepared using this sequence, with the most potent inhibitor having an IC50 value of 1.6 nM.

  DOI：

  10.1021/ja0676004
• 作为产物：
  描述：

  (6S)-2-[4-(4-fluorophenyl)-imidazol-1-yl]-3-methylbut-3-en-1-ol 在 Pd₂(dibenzylideneacetone)2*CHCl₃ 、 [RhCl(coe)2]2 4-二甲氨基吡啶 、 Oxone 、 copper(l) iodide 、 溴 、 N,N-二异丙基乙胺 、 三苯基膦 、 lithium chloride 、 magnesium bromide 、 三环己基膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 68.25h， 生成 (5S,6S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(4-fluoro-phenyl)-3-(2-methanesulfonyl-pyrimidin-4-yl)-6-methyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole
  参考文献：
  名称：

  Synthesis of Potent Bicyclic Bisarylimidazole c-Jun N-Terminal Kinase Inhibitors by Catalytic C−H Bond Activation

  摘要：

  The efficient preparation of the privileged bicyclic bisarylimidazole kinase inhibitor scaffold was accomplished using rhodium-catalyzed C-H activation and intramolecular alkylation. The key C-H activation/alkylation step represents one of the first evaluations of diastereocontrol in catalyzed C-H activation/olefin alkylation processes. Several inhibitors of JNK3 were prepared using this sequence, with the most potent inhibitor having an IC50 value of 1.6 nM.

  DOI：

  10.1021/ja0676004