(S)-4-((2-(3-chlorophenyl)-2-hydroxyethyl)amino)-3-(4-methyl-6-(4-(piperazin-1-yl)piperidin-1-yl)-1H-benzo[d]imidazol-2-yl)pyridin-2(1H)-one | 1056877-73-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: (S)-4-((2-(3-chlorophenyl)-2-hydroxyethyl)amino)-3-(4-methyl-6-(4-(piperazin-1-yl)piperidin-1-yl)-1H-benzo[d]imidazol-2-yl)pyridin-2(1H)-one
• CAS: 1056877-73-6
• 化学式: C₃₀H₃₆ClN₇O₂
• 分子量: 562.115
• InChiKey: KXEPJGVLEUIQOG-AREMUKBSSA-N

物化性质

• 密度：
  1.39±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  40.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  112.31
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-4-((2-(3-chlorophenyl)-2-hydroxyethyl)amino)-3-(4-methyl-6-(4-(piperazin-1-yl)piperidin-1-yl)-1H-benzo[d]imidazol-2-yl)pyridin-2(1H)-one 、 氯甲酸甲酯 在 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 以80%的产率得到(S)-methyl 4-(1-(2-(4-(2-(3-chlorophenyl)-2-hydroxyethylamino)-2-oxo-1,2-dihydropyridin-3-yl)-4-methyl-1H-benzo[d]imidazol-6-yl)piperidin-4-yl)piperazine-1-carboxylate
  参考文献：
  名称：

  Balancing oral exposure with Cyp3A4 inhibition in benzimidazole-based IGF-IR inhibitors

  摘要：

  3-(Benzimidazol-2-yl)-pyridine-2-one-based ATP competitive inhibitors of Insulin-like Growth Factor 1 Kinase (IGF-IR) were optimized for reduced Cyp3A4 inhibition and improved oral exposure. The use of malonate as methyl anion synthon via SNAr reaction and double decarboxylation under mild conditions is demonstrated. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.05.104
• 作为产物：
  描述：

  tert-butyl (S)-4-(1-(2-(4-((2-(3-chlorophenyl)-2-hydroxyethyl)amino)-2-oxo-1,2-dihydropyridin-3-yl)-4-methyl-1H-benzo[d]imidazol-6-yl)piperidin-4-yl)piperazine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-4-((2-(3-chlorophenyl)-2-hydroxyethyl)amino)-3-(4-methyl-6-(4-(piperazin-1-yl)piperidin-1-yl)-1H-benzo[d]imidazol-2-yl)pyridin-2(1H)-one
  参考文献：
  名称：

  Balancing oral exposure with Cyp3A4 inhibition in benzimidazole-based IGF-IR inhibitors

  摘要：

  3-(Benzimidazol-2-yl)-pyridine-2-one-based ATP competitive inhibitors of Insulin-like Growth Factor 1 Kinase (IGF-IR) were optimized for reduced Cyp3A4 inhibition and improved oral exposure. The use of malonate as methyl anion synthon via SNAr reaction and double decarboxylation under mild conditions is demonstrated. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.05.104