1-(benzyloxycarbonyl)-3-[2-methyl-5-methylsulfonyl-4-(pyrrol-1-yl)-benzoyl]guanidine | 294204-23-2

• 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-(benzyloxycarbonyl)-3-[2-methyl-5-methylsulfonyl-4-(pyrrol-1-yl)-benzoyl]guanidine
• 英文别名: benzyl N-[amino-[(2-methyl-5-methylsulfonyl-4-pyrrol-1-ylbenzoyl)amino]methylidene]carbamate
• CAS: 294204-23-2
• 化学式: C₂₂H₂₂N₄O₅S
• 分子量: 454.506
• InChiKey: GZZAADOJHNPCLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  141
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(benzyloxycarbonyl)-3-[2-methyl-5-methylsulfonyl-4-(pyrrol-1-yl)-benzoyl]guanidine 在 palladium on activated charcoal 氢气 作用下， 以 丙酮 为溶剂， 反应 9.5h， 以95%的产率得到N-(二氨基亚甲基)-2-甲基-5-(甲基磺酰基)-4-(1H-吡咯-1-基)苯甲酰胺
  参考文献：
  名称：

  A Concise and Efficient Synthesis of [2-Methyl-5-methylsulfonyl-4-(pyrrol-1-yl)benzoyl]guanidinium Methanesulfonate (Eniporide)

  摘要：

  A new synthesis of the benzoylguanidine-type Na+/H+ antiporter inhibitor eniporide (7) is described. Starting from 2-bromo-5-fluorotoluene (1), aromatic substituents were introduced by methanesulfonylation, Pd-catalyzed carboxylation with CO, and halogen-pyrrole exchange. Guanidine acylation was performed using Mukaiyama's procedure.

  DOI：

  10.1002/1099-0690(200006)2000:12<2253::aid-ejoc2253>3.0.co;2-q
• 作为产物：
  描述：

  4-fluoro-2-methyl-5-(methylsulfonyl)benzoic acid 在 2-氯-1-甲基吡啶碘化物 、 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 5.0h， 生成 1-(benzyloxycarbonyl)-3-[2-methyl-5-methylsulfonyl-4-(pyrrol-1-yl)-benzoyl]guanidine
  参考文献：
  名称：

  A Concise and Efficient Synthesis of [2-Methyl-5-methylsulfonyl-4-(pyrrol-1-yl)benzoyl]guanidinium Methanesulfonate (Eniporide)

  摘要：

  A new synthesis of the benzoylguanidine-type Na+/H+ antiporter inhibitor eniporide (7) is described. Starting from 2-bromo-5-fluorotoluene (1), aromatic substituents were introduced by methanesulfonylation, Pd-catalyzed carboxylation with CO, and halogen-pyrrole exchange. Guanidine acylation was performed using Mukaiyama's procedure.

  DOI：

  10.1002/1099-0690(200006)2000:12<2253::aid-ejoc2253>3.0.co;2-q

文献信息

• [DE] VERFAHREN ZUR HERSTELLUNG EINES BENZOYLGUANIDINDERIVATES<br/>[EN] METHOD FOR PRODUCING A BENZOYLGUANIDINE DERIVATIVE<br/>[FR] PROCEDE DE PRODUCTION D'UN DERIVE DE BENZOYLGUANIDINE
  申请人：MERCK PATENT GMBH

  公开号：WO2000066552A1

  公开（公告）日：2000-11-09

  Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung des Benzoylgaunidinderivates N- (Diaminomethylen)-2- methyl-5- ( methylsulfonyl)-4- (pyrrol-1-yl)- benzamid mit Struktur (I). Diese Substanz ist ein NHE-1 selektiver Na+/H+-Antiporter Hemmstoff.
• A Concise and Efficient Synthesis of [2-Methyl-5-methylsulfonyl-4-(pyrrol-1-yl)benzoyl]guanidinium Methanesulfonate (Eniporide)
  作者：Manfred Baumgarth、Rolf Gericke

  DOI：10.1002/1099-0690(200006)2000:12<2253::aid-ejoc2253>3.0.co;2-q

  日期：2000.6

  A new synthesis of the benzoylguanidine-type Na+/H+ antiporter inhibitor eniporide (7) is described. Starting from 2-bromo-5-fluorotoluene (1), aromatic substituents were introduced by methanesulfonylation, Pd-catalyzed carboxylation with CO, and halogen-pyrrole exchange. Guanidine acylation was performed using Mukaiyama's procedure.