4-[6-Chloro-1-(2-trimethylsilylethoxymethyl)pyrrolo[2,3-b]pyridin-4-yl]oxy-3,5-difluoroaniline | 1115491-38-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[6-Chloro-1-(2-trimethylsilylethoxymethyl)pyrrolo[2,3-b]pyridin-4-yl]oxy-3,5-difluoroaniline
• CAS: 1115491-38-7
• 化学式: C₁₉H₂₂ClF₂N₃O₂Si
• 分子量: 425.938
• InChiKey: GLKMDWZDYBIEKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.65
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  62.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[6-Chloro-1-(2-trimethylsilylethoxymethyl)pyrrolo[2,3-b]pyridin-4-yl]oxy-3,5-difluoroaniline 在 1% Pd/C 、 氢气 、 三乙胺 作用下， 以 乙醇 为溶剂， 以97%的产率得到3,5-difluoro-4-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]aniline
  参考文献：
  名称：

  Improved Synthesis of the Selective Rho-Kinase Inhibitor 6-Chloro-N4-{3,5-difluoro-4-[(3-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]phenyl}pyrimidin-2,4-diamine

  摘要：

  A highly potent and selective Rho-kinase inhibitor containing a 7-azaindole moiety has been developed at Bayer Schering Pharma. Herein we disclose details of a significantly improved synthesis of the compound in 8.2% overall yield. Key aspects include cost and safety considerations and the uncommon use of a trifluoromethyl group with controllable reactivity as a masked methyl group.

  DOI：

  10.1021/op900260k
• 作为产物：
  描述：

  6-氯-4-硝基-1-[[2-(三甲基甲硅烷基)乙氧基]甲基]-1H-吡咯并[2,3-b]吡啶 、 4-氨基-2,6-二氟苯酚 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 以78%的产率得到4-[6-Chloro-1-(2-trimethylsilylethoxymethyl)pyrrolo[2,3-b]pyridin-4-yl]oxy-3,5-difluoroaniline
  参考文献：
  名称：

  Improved Synthesis of the Selective Rho-Kinase Inhibitor 6-Chloro-N4-{3,5-difluoro-4-[(3-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]phenyl}pyrimidin-2,4-diamine

  摘要：

  A highly potent and selective Rho-kinase inhibitor containing a 7-azaindole moiety has been developed at Bayer Schering Pharma. Herein we disclose details of a significantly improved synthesis of the compound in 8.2% overall yield. Key aspects include cost and safety considerations and the uncommon use of a trifluoromethyl group with controllable reactivity as a masked methyl group.

  DOI：

  10.1021/op900260k