4-((6-Chloro-3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy)-3,5-difluoroaniline | 1203656-90-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-((6-Chloro-3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy)-3,5-difluoroaniline
• 英文别名: 4-[[6-chloro-3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]oxy]-3,5-difluoroaniline
• CAS: 1203656-90-9
• 化学式: C₁₄H₇ClF₅N₃O
• 分子量: 363.674
• InChiKey: BDOGNXJDEFNIBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  63.9
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-((6-Chloro-3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy)-3,5-difluoroaniline 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以7 g的产率得到3,5-difluoro-4-[(3-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：

  4-((6-氯-3-(三氟甲基)-1-((2-(三甲基甲硅烷基)乙氧基)甲基)-1H-吡咯并 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 4-((6-Chloro-3-(trifluoromethyl)-1H-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

文献信息

• Improved Synthesis of the Selective Rho-Kinase Inhibitor 6-Chloro-<i>N</i>4-{3,5-difluoro-4-[(3-methyl-1<i>H</i>-pyrrolo[2,3-<i>b</i>]pyridin-4-yl)oxy]phenyl}pyrimidin-2,4-diamine
  作者：Hartmut Schirok、Holger Paulsen、Walter Kroh、Gang Chen、Ping Gao

  DOI：10.1021/op900260k

  日期：2010.1.15

  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.