7-methyl-3-[4-[2-(2-1H-tetrazol-5-yl)-5-methyl pyrrolyl]-benzyl]-2-propyl-3H-imidazo[4,5-b]pyridine hydrochloride | 142014-85-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 7-methyl-3-[4-[2-(2-1H-tetrazol-5-yl)-5-methyl pyrrolyl]-benzyl]-2-propyl-3H-imidazo[4,5-b]pyridine hydrochloride
• 英文别名: 7-methyl-3-[4-[5-methyl-2-(1H-tetrazol-5-yl)-1-pyrrolyl]benzyl]-2-propyl-3H-imidazo[4,5-b]pyridine hydrochloride；7-methyl-3-[[4-[2-methyl-5-(2H-tetrazol-5-yl)pyrrol-1-yl]phenyl]methyl]-2-propylimidazo[4,5-b]pyridine;hydrochloride
• CAS: 142014-85-5
• 化学式: C₂₃H₂₄N₈*ClH
• 分子量: 448.958
• InChiKey: MEPMWENLEOIZPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  90.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  7-methyl-3-[4-[2-(2-1H-tetrazol-5-yl)-5-methyl pyrrolyl]-benzyl]-2-propyl-3H-imidazo[4,5-b]pyridine 在 盐酸 作用下， 以 水 、 异丙醇 为溶剂， 反应 3.0h， 以85%的产率得到7-methyl-3-[4-[2-(2-1H-tetrazol-5-yl)-5-methyl pyrrolyl]-benzyl]-2-propyl-3H-imidazo[4,5-b]pyridine hydrochloride
  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

• Imidazole derivatives, potent and selective antagonists of angiotensin II receptor
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0480204B1

  公开（公告）日：1996-03-20
• US5210092A
  申请人：——

  公开号：US5210092A

  公开（公告）日：1993-05-11
• US5215994A
  申请人：——

  公开号：US5215994A

  公开（公告）日：1993-06-01
• 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.