1-(4-methanesulfonyloxymethylphenyl)-5-methylpyrrole-2-carbonitrile | 142015-67-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(4-methanesulfonyloxymethylphenyl)-5-methylpyrrole-2-carbonitrile
• 英文别名: [4-(2-cyano-5-methylpyrrol-1-yl)phenyl]methyl methanesulfonate
• CAS: 142015-67-6
• 化学式: C₁₄H₁₄N₂O₃S
• 分子量: 290.343
• InChiKey: RYZHHBFGOJBNIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  80.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-methanesulfonyloxymethylphenyl)-5-methylpyrrole-2-carbonitrile 在 盐酸 、 sodium azide 、 铁粉 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 27.75h， 生成 7-methyl-3-[4-[2-(2-1H-tetrazol-5-yl)-5-methyl pyrrolyl]-benzyl]-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：

  苯佐卡因 在 吡啶 、 盐酸 、 sodium tetrahydroborate 、 正庚烷 、 溶剂黄146 、 乙酸乙酯 、 甲基磺酰氯 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 13.5h， 生成 1-(4-methanesulfonyloxymethylphenyl)-5-methylpyrrole-2-carbonitrile 、
  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

• Angiotenin II antagonizing heterocyclic derivatives
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US05215994A1

  公开（公告）日：1993-06-01

  The invention relates to compounds of the formula ##STR1## wherein ##STR2## represents a condensed or uncondensed imidazolyl ring and the rest of the variables are as defined in the specification. They are angiotensin II antagonists useful for treating hypertension, etc..

  该发明涉及以下式的化合物：##STR1## 其中##STR2##代表一个紧凑或非紧凑的咪唑环，其余变量如规范中所定义。它们是用于治疗高血压等的抗血管紧张素II受体拮抗剂。
• Angiotensin II antagonizing heterocyclic derivatives
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US05210092A1

  公开（公告）日：1993-05-11

  The invention concerns compounds of the formula ##STR1## represents a condensed or uncondensed imidazolyl ring and the rest of the variables are defined in the specification. They are angiotensin II antagonists useful for treating hypertension, etc.

  该发明涉及公式为##STR1##的化合物，其中R1和R2分别表示紧缩或未紧缩的咪唑基环，其余变量在规范中定义。它们是血管紧张素II拮抗剂，可用于治疗高血压等疾病。
• 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