5-Chloro-3-(1-methyl-piperidin-4-yl)-furo[3,2-b]pyridine | 666178-98-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡啶类
• 英文名称: 5-Chloro-3-(1-methyl-piperidin-4-yl)-furo[3,2-b]pyridine
• 英文别名: Furo[3,2-b]pyridine, 5-chloro-3-(1-methyl-4-piperidinyl)-；5-chloro-3-(1-methylpiperidin-4-yl)furo[3,2-b]pyridine
• CAS: 666178-98-9
• 化学式: C₁₃H₁₅ClN₂O
• 分子量: 250.728
• InChiKey: SECHQQXCCFWWGV-UHFFFAOYSA-N

物化性质

• 沸点：
  350.0±42.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Chloro-3-(1-methyl-piperidin-4-yl)-furo[3,2-b]pyridine 在 吡啶 、 盐酸 、 tris(dibenzylideneacetone)dipalladium (0) 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 2-Chloro-4-fluoro-N-[3-(1-methyl-piperidin-4-yl)-furo[3,2-b]pyridin-5-yl]-benzamide
  参考文献：
  名称：

  Substituted furo[3,2-b]pyridines: novel bioisosteres of 5-HT1F receptor agonists

  摘要：

  Synthesis and evaluation of a series of 2,3,5- and 3,5-substituted furo[3,2-b]pyridines were undertaken in order to investigate their utility as bioisosteres of 5-HTIF receptor agonist indole analogues, 1-3. The replacement proved to be effective, providing compounds with similar 5-HTIF receptor affinity and improved selectivity when compared with the indole analogues. Through these studies we identified 4-fluoro-N-[3-(1-methyl-piperidin-4-yl)-furo[3,2-b]pyridin-5-yl]-benzamide (5), a potent and selective 5-HTIF receptor agonist with the potential to treat acute migraine. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.091
• 作为产物：
  描述：

  4-(5-Chloro-furo[3,2-b]pyridin-3-yl)-piperidine-1-carboxylic acid tert-butyl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以61%的产率得到5-Chloro-3-(1-methyl-piperidin-4-yl)-furo[3,2-b]pyridine
  参考文献：
  名称：

  Substituted furo[3,2-b]pyridines: novel bioisosteres of 5-HT1F receptor agonists

  摘要：

  Synthesis and evaluation of a series of 2,3,5- and 3,5-substituted furo[3,2-b]pyridines were undertaken in order to investigate their utility as bioisosteres of 5-HTIF receptor agonist indole analogues, 1-3. The replacement proved to be effective, providing compounds with similar 5-HTIF receptor affinity and improved selectivity when compared with the indole analogues. Through these studies we identified 4-fluoro-N-[3-(1-methyl-piperidin-4-yl)-furo[3,2-b]pyridin-5-yl]-benzamide (5), a potent and selective 5-HTIF receptor agonist with the potential to treat acute migraine. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.091