2-(1-丙基-4-哌啶基)-1H-苯并咪唑-7-羧酰胺丁二酸 | 943650-25-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 2-(1-丙基-4-哌啶基)-1H-苯并咪唑-7-羧酰胺丁二酸
• 英文名称: 2-(1-propyl-4-piperidinyl)-1H-benzimidazole-4-carboxamide succinate salt
• 英文别名: ABT-472；2-(1-Propylpiperidin-4-yl)-1H-benzo[d]imidazole-7-carboxamide succinate；butanedioic acid;2-(1-propylpiperidin-4-yl)-1H-benzimidazole-4-carboxamide
• CAS: 943650-25-7
• 化学式: C₄H₆O₄*C₁₆H₂₂N₄O
• 分子量: 404.466
• InChiKey: GWFBXGWIRCSOAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.19
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  150
• 氢给体数：
  4
• 氢受体数：
  7

安全信息

• 海关编码：
  2934999090

反应信息

• 作为产物：
  描述：

  2-amino-3-nitrobenzoyl chloride 在 盐酸 、 ammonium hydroxide 、 氢气 、 溶剂黄146 作用下， 以 N-甲基吡咯烷酮 、 甲醇 、 乙醇 、 水 、 乙酸乙酯 为溶剂， 30.0~60.0 ℃ 、377.13 kPa 条件下， 反应 9.17h， 生成 2-(1-丙基-4-哌啶基)-1H-苯并咪唑-7-羧酰胺丁二酸
  参考文献：
  名称：

  Process Development for ABT-472, a Benzimidazole PARP Inhibitor

  摘要：

  A nine-step convergent process was developed for the synthesis of ABT-472, a benzimidazole PARP inhibitor. The identity and origin of several impurities were determined, and the process was modified to reduce or eliminate these impurities. A number of safety and control issues were investigated. The original synthesis was shortened to 9 steps and streamlined while maintaining a convergent strategy. A stable salt was selected, and control of the API solid form was established. The process was successfully scaled up to provide 8.5 kg of final product of > 99% purity in 33% yield over 9 steps.

  DOI：

  10.1021/op7000194

文献信息

• Process Development for ABT-472, a Benzimidazole PARP Inhibitor
  作者：Jufang H. Barkalow、Jeffrey Breting、Bruce J. Gaede、Anthony R. Haight、Rodger Henry、Brian Kotecki、Jianzhang Mei、Kurt B. Pearl、Jason S. Tedrow、Shekhar K. Viswanath

  DOI：10.1021/op7000194

  日期：2007.7.1

  A nine-step convergent process was developed for the synthesis of ABT-472, a benzimidazole PARP inhibitor. The identity and origin of several impurities were determined, and the process was modified to reduce or eliminate these impurities. A number of safety and control issues were investigated. The original synthesis was shortened to 9 steps and streamlined while maintaining a convergent strategy. A stable salt was selected, and control of the API solid form was established. The process was successfully scaled up to provide 8.5 kg of final product of > 99% purity in 33% yield over 9 steps.