2-methyl-4-(1-methyl-1H-benzimidazol-2-yl)-6-nitrobenzenamine | 1345840-05-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-methyl-4-(1-methyl-1H-benzimidazol-2-yl)-6-nitrobenzenamine
• 英文别名: 2-Methyl-4-(1-methylbenzimidazol-2-yl)-6-nitroaniline
• CAS: 1345840-05-2
• 化学式: C₁₅H₁₄N₄O₂
• 分子量: 282.302
• InChiKey: ZAJRXPOWCCDIHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  89.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-4-(1-methyl-1H-benzimidazol-2-yl)-6-nitrobenzenamine 在 sodium dithionite 、 sodium hydride 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 25.0h， 生成 替米沙坦甲酯
  参考文献：
  名称：

  Highly practical and cost-efficient synthesis of telmisartan: an antihypertensive drug

  摘要：

  A novel and cost-efficient strategy for synthesis of an antihypertensive drug telmisartan, a substituted bis-benzimidazole derivative, is described. The key strategy is the construction of bis-benzimidazole 4 by reductive cyclization of o-nitroanilines 11 with butyl aldehyde and cyclocondensation of aromatic aldehydes 9 with o-phenylenediamine, then N-alkylation is allowed to give the target compound telmisartan after hydrolysis. The simple operation and workup procedure, along with the low production costs, make it suitable for industrial production and will benefits those with cardiovascular disease. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.056
• 作为产物：
  描述：

  4-甲氧基-3-甲基-5-硝基苯甲醛 在 氨 、 双氧水 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 2-methyl-4-(1-methyl-1H-benzimidazol-2-yl)-6-nitrobenzenamine
  参考文献：
  名称：

  Highly practical and cost-efficient synthesis of telmisartan: an antihypertensive drug

  摘要：

  A novel and cost-efficient strategy for synthesis of an antihypertensive drug telmisartan, a substituted bis-benzimidazole derivative, is described. The key strategy is the construction of bis-benzimidazole 4 by reductive cyclization of o-nitroanilines 11 with butyl aldehyde and cyclocondensation of aromatic aldehydes 9 with o-phenylenediamine, then N-alkylation is allowed to give the target compound telmisartan after hydrolysis. The simple operation and workup procedure, along with the low production costs, make it suitable for industrial production and will benefits those with cardiovascular disease. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.056

文献信息

• Tetrahedron 2012, 68, 2509-2512
  作者：

  DOI：——

  日期：——
• Highly practical and cost-efficient synthesis of telmisartan: an antihypertensive drug
  作者：Ping Wang、Guo-jun Zheng、Ya-ping Wang、Xiang-jing Wang、He-geng Wei、Wen-sheng Xiang

  DOI：10.1016/j.tet.2012.01.056

  日期：2012.3

  A novel and cost-efficient strategy for synthesis of an antihypertensive drug telmisartan, a substituted bis-benzimidazole derivative, is described. The key strategy is the construction of bis-benzimidazole 4 by reductive cyclization of o-nitroanilines 11 with butyl aldehyde and cyclocondensation of aromatic aldehydes 9 with o-phenylenediamine, then N-alkylation is allowed to give the target compound telmisartan after hydrolysis. The simple operation and workup procedure, along with the low production costs, make it suitable for industrial production and will benefits those with cardiovascular disease. (C) 2012 Elsevier Ltd. All rights reserved.