5-chloro-6-methylimidazo[1,2-a]pyridine | 442129-34-2

• 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: 5-chloro-6-methylimidazo[1,2-a]pyridine
• 英文别名: 5-Chloro-6-methylimidazo[1,2-a]pyridine
• CAS: 442129-34-2
• 化学式: C₈H₇ClN₂
• 分子量: 166.61
• InChiKey: MFUMHGNYUHPRDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  17.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-chloro-6-methylimidazo[1,2-a]pyridine 、 pyridin-2-ylzinc(II) bromide 在 2-双环己基膦-2',6'-双(二甲基氨基)-1,1'-联苯 、 palladium diacetate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以22%的产率得到6-methyl-5-(pyridin-2-yl)imidazo[1,2-a]pyridine
  参考文献：
  名称：

  ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES

  摘要：

  一个具有下面显示的第一配体L的化合物的化学式I被披露。

  公开号：

  US20190067601A1
• 作为产物：
  描述：

  氯乙醛 、 6-氯-5-甲基-2-吡啶胺 以 乙醇 为溶剂， 反应 18.0h， 以85%的产率得到5-chloro-6-methylimidazo[1,2-a]pyridine
  参考文献：
  名称：

  ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES

  摘要：

  一个具有下面显示的第一配体L的化合物的化学式I被披露。

  公开号：

  US20190067601A1

文献信息

• [EN] HETEROAROMATIC COMPOUNDS AND THEIR USE AS DOPAMINE D1 LIGANDS<br/>[FR] COMPOSÉS HÉTÉROAROMATIQUES ET LEUR UTILISATION COMME LIGANDS DE LA DOPAMINE D1
  申请人：PFIZER

  公开号：WO2014072881A1

  公开（公告）日：2014-05-15

  The present invention provides, in part, compounds of Formula I: and pharmaceutically acceptable salts thereof and N-oxides thereof; processes and intermediates for preparation of; and compositions and uses thereof. The present invention further provides D1 agonists with reduced D1R desensitization, D1 agonists with a reduced β- arrestin recruitment activity relative to Dopamine, D1 agonists interacting significantly with the Ser188 but not significantly with the Ser202 of a D1R when binding to the D1R, D1 agonists interacting less strongly with the Asp103 and interacting less strongly with the Ser198 of a D1R when binding to the D1R, and their uses.

  本发明部分提供了化合物I的公式：及其药学上可接受的盐和N-氧化物；制备的过程和中间体；以及其组合物和用途。本发明进一步提供了具有减少D1R耐受性的D1激动剂，相对于多巴胺具有减少β-阿雷斯汀招募活性的D1激动剂，当结合到D1R时与D1R的Ser188显著相互作用但与Ser202的相互作用不显著的D1激动剂，当结合到D1R时与D1R的Asp103相互作用较弱并且与Ser198相互作用较弱的D1激动剂，以及它们的用途。
• Heteroaromatic Compounds and their Use as Dopamine D1 Ligands
  申请人：PFIZER INC.

  公开号：US20150344490A1

  公开（公告）日：2015-12-03

  The present invention provides, in part, compounds of Formula I: and pharmaceutically acceptable salts thereof and N-oxides thereof; processes and intermediates for preparation of; and compositions and uses thereof. The present invention further provides D1 agonists with reduced D1R desensitization, D1 agonists with a reduced β-arrestin recruitment activity relative to Dopamine, D1 agonists interacting significantly with the Ser188 but not significantly with the Ser202 of a D1R when binding to the D1R, D1 agonists interacting less strongly with the Asp103 and interacting less strongly with the Ser198 of a D1R when binding to the D1R, and their uses.

  本发明提供了部分式I的化合物及其药学上可接受的盐和N-氧化物；其制备的过程和中间体；以及其组合物和用途。本发明还提供了具有降低D1R失效的D1激动剂，具有相对于多巴胺降低β-阻滞素招募活性的D1激动剂，当结合到D1R时与Ser188显著相互作用但与Ser202显著不相互作用的D1激动剂，当结合到D1R时与Asp103相互作用较弱且与Ser198相互作用较弱的D1激动剂，以及它们的用途。
• Synthesis of 5-bromo-6-methyl imidazopyrazine, 5-bromo and 5-chloro-6-methyl imidazopyridine using electron density surface maps to guide synthetic strategy
  作者：Anthony R. Harris、Deane M. Nason、Elizabeth M. Collantes、Wenjian Xu、Yushi Chi、Zhihan Wang、Bingzhi Zhang、Qingjian Zhang、David L. Gray、Jennifer E. Davoren

  DOI：10.1016/j.tet.2011.08.090

  日期：2011.11

  Small heteroaromatic rings are valuable monomers in drug discovery that can enable rapid access to novel and desirable chemical space. Installation of a synthetic handle on a heteroaromatic core may be difficult if steric and electronic factors are not in alignment with the desired transformation. Described are practical routes for the construction of 5-bromo-6-methyl imidazopyrazine (1) as well as 5-bromo and 5-chloro-6-methyl imidazopyridines (2a and 2b), which were developed using electron density surface maps encoded with ionization potential to guide synthetic strategy. (C) 2011 Elsevier Ltd. All rights reserved.
• HETEROAROMATIC COMPOUNDS AND THEIR USE AS DOPAMINE D1 LIGANDS
  申请人：Pfizer Inc.

  公开号：EP2917219B1

  公开（公告）日：2017-09-27
• US9617275B2
  申请人：——

  公开号：US9617275B2

  公开（公告）日：2017-04-11