N-(2-amino-3-carbamoylphenyl)-1-propylpiperidine-4-carboxamide;hydrochloride

• 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: N-(2-amino-3-carbamoylphenyl)-1-propylpiperidine-4-carboxamide;hydrochloride
• 化学式: C₁₆H₂₄N₄O₂*ClH
• 分子量: 340.853
• InChiKey: QFEUFZABJMKGRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.85
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  101.45
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-(2-amino-3-carbamoylphenyl)-1-propylpiperidine-4-carboxamide;hydrochloride 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 4.0h， 以86%的产率得到2-(1-丙基-4-哌啶基)-1H-苯并咪唑-7-羧酰胺
  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
• 作为产物：
  描述：

  2-amino-3-nitrobenzoyl chloride 在 盐酸 、 ammonium hydroxide 、 氢气 作用下， 以 N-甲基吡咯烷酮 、 乙醇 、 水 、 乙酸乙酯 为溶剂， 30.0~50.0 ℃ 、377.13 kPa 条件下， 反应 1.67h， 生成 N-(2-amino-3-carbamoylphenyl)-1-propylpiperidine-4-carboxamide;hydrochloride
  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