3-nitro-5-(pyrrolidine-1-carboxamido)benzoic acid | 1616474-07-7

• 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: 3-nitro-5-(pyrrolidine-1-carboxamido)benzoic acid
• 英文别名: 3-Nitro-5-(pyrrolidine-1-carbonylamino)benzoic acid
• CAS: 1616474-07-7
• 化学式: C₁₂H₁₃N₃O₅
• 分子量: 279.252
• InChiKey: QGESEPWVBQFXAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-nitro-5-(pyrrolidine-1-carboxamido)benzoic acid 在 tris-(dibenzylideneacetone)dipalladium(0) 、 5%-palladium/activated carbon 、 氢气 、 potassium carbonate 、 三乙胺 、 2-二环己基磷-2,4,6-三异丙基联苯 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 甲醇 、 叔丁醇 为溶剂， -15.0~20.0 ℃ 、101.33 kPa 条件下， 反应 22.5h， 生成 N-(3-((2-(piperidin-1-yl)ethyl)carbamoyl)-5-((4-(3-(pyridin-3-ylmethoxy)phenyl)-7-tosyl-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
• 作为产物：
  描述：

  ethyl 3-nitro-5-(pyrrolidine-1-carboxamido)benzoate 在 sodium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 1.0h， 以86%的产率得到3-nitro-5-(pyrrolidine-1-carboxamido)benzoic acid
  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