ethyl 5-methylimidazo[1,2-a]pyridine-3-carboxylate | 196880-15-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: ethyl 5-methylimidazo[1,2-a]pyridine-3-carboxylate
• 英文别名: 3-carbethoxy-5-methylimidazo[1,2-a]-pyridine
• CAS: 196880-15-6
• 化学式: C₁₁H₁₂N₂O₂
• 分子量: 204.228
• InChiKey: JEMUQVAOZYUVIU-UHFFFAOYSA-N

物化性质

• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 5-methylimidazo[1,2-a]pyridine-3-carboxylate 在 N-氯代丁二酰亚胺 、 三氟乙酸 作用下， 以 乙酸乙酯 为溶剂， 反应 168002.0h， 生成
  参考文献：
  名称：

  A Practical Synthesis of the Chronic Renal Disease Agent, 4,5-Dihydro-3H-1,4,8b-triazaacenaphthylen-3-one Derivatives, Using Regioselective Chlorination of Ethyl 5-methylimidazo[1,2-a]pyridine-3-carboxylate with N-Chlorosuccinimide

  摘要：

  A convenient synthesis of the chronic renal disease agent, trifluoro-N-[4-(3-oxo-3,5-dihydro-4H-1,4,8b-triazaacenaphthylen-4yl)butyl]methanesulfonamide (1a), for large scale has been developed via ethyl 5-(chloromethyl)imidazo[1,2-a]pyridine-3-carboxylate (3), which was given by the regioselective chlorination of ethyl 5-methylimidazo[1,2-a]pyridine-3-carboxlate (6) with N-chlorosuccinimide (NCS) using AcOEt as a solvent in 83% yield. The condensation of 3 and primary amines gave 4,5-dihydro-3H-1,4,8b-triazaacenaphthylen-3-one derivatives (1) in good yields. The present synthesis of 1a was accomplished in five steps from 2-amino-6-methylpyridine (4) without requiring a chromatographic method. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00709-2
• 作为产物：
  描述：

  2-氨基-6-甲基吡啶 、 (氯甲酰基)乙酸乙酯 以 乙醇 为溶剂， 以62%的产率得到ethyl 5-methylimidazo[1,2-a]pyridine-3-carboxylate
  参考文献：
  名称：

  Reactions with N-Chlorosuccinimide of Various 5-Methylimidazo[1,2-a]pyridine Derivatives with an Electron-withdrawing Group Substituted at the 3-Position

  摘要：

  Chlorination reactions using N-chlorosuccinimide (NCS) was investigated for various 5-methylimidazo[1,2-a]pyridine derivatives with an electron-withdrawing group substituted at the 3-position. These reactions showed different results, and by examining these, we proposed a reaction mechanism via the appropriate 3-halogenoimidazo[1,2-a]pyridium compounds as the reaction intermediates.

  DOI：

  10.3987/com-00-9063

文献信息

• Tricyclic compounds, their production and use
  申请人：——

  公开号：US20010051631A1

  公开（公告）日：2001-12-13

  Tricyclic compound of the formula: 1 wherein ring A is a nitrogen-containing heterocyclic ring, having two nitrogen atoms as the hetero-atoms, which is optionally substituted with oxo or thioxo; ring Q may optionally be substituted; Y is an optionally substituted hydrocarbon group, an optionally substituted hydroxyl group or an optionally substituted mecapto group, excluding for methyl group as Y; R 1 is a hydrogen atom, a halogen atom, an optionally substituted hydrocarbon group or an acyl group, or a salt thereof, having excellent PDGF-inhibiting activities, antihypertensive activities, activities of ameliorating renal diseases and activities of lowering lipid level.

  式子1中的三环化合物：其中环A是含有两个氮原子作为杂原子的含氮杂环，可选择性地用氧代或硫代取代; 环Q可以选择性地被取代; Y是可选择性取代的碳氢基团，可选择性取代的羟基或可选择性取代的巯基，但不包括甲基基团作为Y; R1是氢原子，卤素原子，可选择性取代的碳氢基团或酰基，或其盐，具有优异的PDGF抑制活性，降压活性，改善肾脏疾病活性和降低脂质水平活性。
• US5958942
  申请人：——

  公开号：——

  公开（公告）日：——
• US05958942
  申请人：——

  公开号：——

  公开（公告）日：——
• JPH09249666A
  申请人：——

  公开号：JPH09249666A

  公开（公告）日：1997-09-22
• US5958942A
  申请人：——

  公开号：US5958942A

  公开（公告）日：1999-09-28