2-(3-aminophenyl)-N-(2-(piperidin-1-yl)ethyl)acetamide | 1498710-52-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(3-aminophenyl)-N-(2-(piperidin-1-yl)ethyl)acetamide
• 英文别名: 2-(3-aminophenyl)-N-(2-piperidin-1-ylethyl)acetamide
• CAS: 1498710-52-3
• 化学式: C₁₅H₂₃N₃O
• 分子量: 261.367
• InChiKey: PYCWMYCLQMPEQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  58.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-aminophenyl)-N-(2-(piperidin-1-yl)ethyl)acetamide 、 2-chloro-4-(3-(pyridin-3-ylmethoxy)phenyl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine 在 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 叔丁醇 为溶剂， 反应 16.0h， 以72%的产率得到N-(2-(piperidin-1-yl)ethyl)-2-(3-((4-(3-(pyridin-3-ylmethoxy)phenyl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)phenyl)acetamide
  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-硝基苯乙酸 在 氯化亚砜 、 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 7.0h， 生成 2-(3-aminophenyl)-N-(2-(piperidin-1-yl)ethyl)acetamide
  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.