N-(3-((2-(piperidin-1-yl)ethyl)carbamoyl)-5-((4-(3-(pyridin-3-ylmethoxy)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)phenyl)pyrrolidine-1-carboxamide | 1616474-28-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N-(3-((2-(piperidin-1-yl)ethyl)carbamoyl)-5-((4-(3-(pyridin-3-ylmethoxy)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)phenyl)pyrrolidine-1-carboxamide
• 英文别名: N-[3-(2-piperidin-1-ylethylcarbamoyl)-5-[[4-[3-(pyridin-3-ylmethoxy)phenyl]-7H-pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]pyrrolidine-1-carboxamide
• CAS: 1616474-28-2
• 化学式: C₃₇H₄₁N₉O₃
• 分子量: 659.791
• InChiKey: KFQHBFMDOPPOOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  49
• 可旋转键数：
  11
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-氯甲基吡啶盐酸盐 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 tris-(dibenzylideneacetone)dipalladium(0) 、 四(三苯基膦)钯 、 potassium acetate 、 sodium carbonate 、 potassium carbonate 、 caesium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 84.0h， 生成 N-(3-((2-(piperidin-1-yl)ethyl)carbamoyl)-5-((4-(3-(pyridin-3-ylmethoxy)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)phenyl)pyrrolidine-1-carboxamide
  参考文献：
  名称：

  Synthesis and biological evaluation of substituted 2-anilino-7H-pyrrolopyrimidines as PDK1 inhibitors

  摘要：

  An efficient and scalable route for a series of novel substituted 2-anilino-7H-pyrrolopyrimidine compounds as potential inhibitors of PDK1, an important regulator of the PI3K/Akt pathway that is dysregulated in many cancers, was developed and is described. The synthetic strategy was designed around Suzuki and Buchwald-Hartwig cross-couplings of a boronate fragment and various customised anilines sequentially with 2,4-dichloro-7-tosyl-7H-pyrrolopyrimidine. All fragments were constructed separately and cross-coupled to provide access to a range of novel compounds. Biological evaluation of these was undertaken, with modest inhibition observed. Crown Copyright (C) 2014 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.033

文献信息

• Synthesis and biological evaluation of substituted 2-anilino-7H-pyrrolopyrimidines as PDK1 inhibitors
  作者：Nathan J. O'Brien、Martin Brzozowski、David J.D. Wilson、Leslie W. Deady、Belinda M. Abbott

  DOI：10.1016/j.tet.2014.05.033

  日期：2014.8

  An efficient and scalable route for a series of novel substituted 2-anilino-7H-pyrrolopyrimidine compounds as potential inhibitors of PDK1, an important regulator of the PI3K/Akt pathway that is dysregulated in many cancers, was developed and is described. The synthetic strategy was designed around Suzuki and Buchwald-Hartwig cross-couplings of a boronate fragment and various customised anilines sequentially with 2,4-dichloro-7-tosyl-7H-pyrrolopyrimidine. All fragments were constructed separately and cross-coupled to provide access to a range of novel compounds. Biological evaluation of these was undertaken, with modest inhibition observed. Crown Copyright (C) 2014 Published by Elsevier Ltd. All rights reserved.