N-phenyl-4-(3-(pyridin-3-ylmethoxy)phenyl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine | 1616474-21-5

• 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-phenyl-4-(3-(pyridin-3-ylmethoxy)phenyl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine
• CAS: 1616474-21-5
• 化学式: C₃₁H₂₅N₅O₃S
• 分子量: 547.637
• InChiKey: COSQQJPLPQFJGM-UHFFFAOYSA-N

物化性质

• 沸点：
  798.0±70.0 °C(predicted)
• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.36
• 重原子数：
  40.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  99.0
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-phenyl-4-(3-(pyridin-3-ylmethoxy)phenyl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine 在 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以95%的产率得到N-phenyl-4-(3-(pyridin-3-ylmethoxy)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine
  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
• 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 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 81.0h， 生成 N-phenyl-4-(3-(pyridin-3-ylmethoxy)phenyl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine
  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