N-[[4-(2-cyano-5-methylpyrrol-1-yl)phenyl]methyl]-N-(4-methyl-3-nitropyridin-2-yl)butanamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: N-[[4-(2-cyano-5-methylpyrrol-1-yl)phenyl]methyl]-N-(4-methyl-3-nitropyridin-2-yl)butanamide
• 化学式: C₂₃H₂₃N₅O₃
• 分子量: 417.467
• InChiKey: LILXBPUQANGIJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  105.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-[[4-(2-cyano-5-methylpyrrol-1-yl)phenyl]methyl]-N-(4-methyl-3-nitropyridin-2-yl)butanamide 在 铁粉 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以45.5 kg的产率得到3-[4-[1-(2-cyano-5-methyl pyrrolyl)]benzyl]-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine
  参考文献：
  名称：

  Pilot Scale Synthesis of a Novel Nonpeptide Angiotensin II Receptor Antagonist

  摘要：

  FR143187 is a novel nonpeptide angiotensin II receptor antagonist under development at Fujisawa Pharmaceutical Co. for the treatment of hypertension, Development of a process for preparation on a large scale is described. The optimized process is 10 steps in length and uses only commercially available materials for each step. Efficient methylation of the 2-position of a pyrrole derivative was achieved by reduction of a Mannich base via the quaternary ammonium salt, Selective cyanation directed by a soh:ent effect was also investigated. Process improvement efforts focused on optimized reaction conditions for each step, leading to a high-quality product according to a new and concise synthetic route.

  DOI：

  10.1021/op9800055
• 作为产物：
  描述：

  2-氨基-3-硝基-4-甲基吡啶 在 potassium carbonate 、 N,N-二甲基苯胺 、 sodium hydroxide 作用下， 以 甲苯 为溶剂， 反应 21.75h， 生成 N-[[4-(2-cyano-5-methylpyrrol-1-yl)phenyl]methyl]-N-(4-methyl-3-nitropyridin-2-yl)butanamide
  参考文献：
  名称：

  Pilot Scale Synthesis of a Novel Nonpeptide Angiotensin II Receptor Antagonist

  摘要：

  FR143187 is a novel nonpeptide angiotensin II receptor antagonist under development at Fujisawa Pharmaceutical Co. for the treatment of hypertension, Development of a process for preparation on a large scale is described. The optimized process is 10 steps in length and uses only commercially available materials for each step. Efficient methylation of the 2-position of a pyrrole derivative was achieved by reduction of a Mannich base via the quaternary ammonium salt, Selective cyanation directed by a soh:ent effect was also investigated. Process improvement efforts focused on optimized reaction conditions for each step, leading to a high-quality product according to a new and concise synthetic route.

  DOI：

  10.1021/op9800055

文献信息

• Pilot Scale Synthesis of a Novel Nonpeptide Angiotensin II Receptor Antagonist
  作者：Atsuhiko Zanka、Masanori Nishiwaki、Yasuhiro Morinaga、Takayuki Inoue

  DOI：10.1021/op9800055

  日期：1998.7.1

  FR143187 is a novel nonpeptide angiotensin II receptor antagonist under development at Fujisawa Pharmaceutical Co. for the treatment of hypertension, Development of a process for preparation on a large scale is described. The optimized process is 10 steps in length and uses only commercially available materials for each step. Efficient methylation of the 2-position of a pyrrole derivative was achieved by reduction of a Mannich base via the quaternary ammonium salt, Selective cyanation directed by a soh:ent effect was also investigated. Process improvement efforts focused on optimized reaction conditions for each step, leading to a high-quality product according to a new and concise synthetic route.