1-butyl-2-isopropylamino-1H-benzo[d]imidazole-5-carboxylic acid methyl ester | 1329121-70-1

• 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: 1-butyl-2-isopropylamino-1H-benzo[d]imidazole-5-carboxylic acid methyl ester
• 英文别名: Methyl 1-butyl-2-(propan-2-ylamino)benzimidazole-5-carboxylate；methyl 1-butyl-2-(propan-2-ylamino)benzimidazole-5-carboxylate
• CAS: 1329121-70-1
• 化学式: C₁₆H₂₃N₃O₂
• 分子量: 289.378
• InChiKey: TZSBBTHSSBUDLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  56.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 甲酸铵 、 sodium methylate 、 三乙胺 、 锌 、 碘甲烷 作用下， 以 甲醇 、 乙腈 为溶剂， 60.0~90.0 ℃ 、400.01 kPa 条件下， 反应 0.45h， 生成 1-butyl-2-isopropylamino-1H-benzo[d]imidazole-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Novel approach towards 2-substituted aminobenzimidazoles on imidazolium ion tag under focused microwave irradiation

  摘要：

  We have developed an efficient, parallel synthesis of 2-substituted aminobenzimidazoles via intramolecular ring closing reactions of imidazolium ion tag immobilized o-phenylenediamine with various isothiocyanates. The methodology is based on the attachment of 4-fluoro-3-nitro benzoic acid into the imidazolium ion tag, which enables the SNAr reactions with different amines followed by neutral reduction to furnish o-phenylenediamines under microwave irradiation. The substituted isothiocyanates are reacted with o-phenylenediamines to form monothiourea, which is further activated by methyl iodide to undergo desulfurization in one pot manner. The ionic liquid bound 2-substituted aminobenzimidazoles were finally cleaved from the support with sodium methoxide to generate target compounds in good yields and high purities with two points of structural diversity. This synthetic protocol has promising features of extremely short reaction time, operational simplicity, good yields, as well as widespread applications, leading to a facile and straightforward admittance to structurally diverse 2-substituted aminobenzimidazole analogues with potential bioactivities. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.068

文献信息

• Novel approach towards 2-substituted aminobenzimidazoles on imidazolium ion tag under focused microwave irradiation
  作者：Kaushik Chanda、Barnali Maiti、Wen-Sheng Chung、Chung-Ming Sun

  DOI：10.1016/j.tet.2011.06.068

  日期：2011.8

  We have developed an efficient, parallel synthesis of 2-substituted aminobenzimidazoles via intramolecular ring closing reactions of imidazolium ion tag immobilized o-phenylenediamine with various isothiocyanates. The methodology is based on the attachment of 4-fluoro-3-nitro benzoic acid into the imidazolium ion tag, which enables the SNAr reactions with different amines followed by neutral reduction to furnish o-phenylenediamines under microwave irradiation. The substituted isothiocyanates are reacted with o-phenylenediamines to form monothiourea, which is further activated by methyl iodide to undergo desulfurization in one pot manner. The ionic liquid bound 2-substituted aminobenzimidazoles were finally cleaved from the support with sodium methoxide to generate target compounds in good yields and high purities with two points of structural diversity. This synthetic protocol has promising features of extremely short reaction time, operational simplicity, good yields, as well as widespread applications, leading to a facile and straightforward admittance to structurally diverse 2-substituted aminobenzimidazole analogues with potential bioactivities. (C) 2011 Elsevier Ltd. All rights reserved.