2-(1H-benzo[d]imidazol-2-yl)-N-methyl-N-(2-(pyrrolidin-1-yl)ethyl)acetamide | 1042720-76-2

• 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-(1H-benzo[d]imidazol-2-yl)-N-methyl-N-(2-(pyrrolidin-1-yl)ethyl)acetamide
• CAS: 1042720-76-2
• 化学式: C₁₆H₂₂N₄O
• 分子量: 286.377
• InChiKey: WKLHGFXKCPBRQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.66
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.23
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(1H-benzo[d]imidazol-2-yl)-N-methyl-N-(2-(pyrrolidin-1-yl)ethyl)acetamide 、 2,6-二氯吡啶-3-羰酰氯 在 三乙胺 、 magnesium chloride 作用下， 以 四氢呋喃 为溶剂， 生成 2-chloro-N-methyl-5-oxo-N-(2-pyrrolidin-1-ylethyl)-7H-benzimidazolo[1,2-a][1,8]naphthyridine-6-carboxamide 、 2-chloro-N-methyl-5-oxo-N-(2-(pyrrolidin-1-yl)ethyl)-5,11-dihydrobenzo[4,5]imidazo[1,2-g][1,6]naphthyridine-12-carboxamide
  参考文献：
  名称：

  A novel and efficient synthesis of 3-carboxy-4-oxo-1,8-naphthyridines using magnesium chloride

  摘要：

  A novel and efficient synthesis of 5-oxo-6-carboxy-naphthyridines is reported in this Letter along with a discussion of scope and limitations. Activated 3-nicotinic acids readily acylate the magnesium anion of 2-(benzothiazol-2-yl) or 2-(benzimidazol-2-yl) acetates. The corresponding product can then undergo cyclization spontaneously or under very mild conditions to give the desired naphthyridine products. Only near stoichiometric ratios of reactants are required for this approach and the products are isolated in pure form after a trituration making this an efficient process. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.005