4-(5-Chloro-furo[3,2-b]pyridin-3-yl)-piperidine-1-carboxylic acid tert-butyl ester | 666178-96-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-(5-Chloro-furo[3,2-b]pyridin-3-yl)-piperidine-1-carboxylic acid tert-butyl ester
• 英文别名: Tert-butyl 4-(5-chlorofuro[3,2-b]pyridin-3-yl)piperidine-1-carboxylate；tert-butyl 4-(5-chlorofuro[3,2-b]pyridin-3-yl)piperidine-1-carboxylate
• CAS: 666178-96-7
• 化学式: C₁₇H₂₁ClN₂O₃
• 分子量: 336.818
• InChiKey: GBDBGWRJQUJOOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  Tert-butyl 4-[2-(6-chloro-2-iodopyridin-3-yl)oxyethylidene]piperidine-1-carboxylate 在 sodium formate palladium diacetate 、 n-Bu₄Cl 、 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以60%的产率得到4-(5-Chloro-furo[3,2-b]pyridin-3-yl)-piperidine-1-carboxylic acid tert-butyl ester
  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

文献信息

• Substituted furo[3,2-b]pyridines: novel bioisosteres of 5-HT1F receptor agonists
  作者：Brian M. Mathes、Kevin J. Hudziak、John M. Schaus、Yao-Chang Xu、David L. Nelson、David B. Wainscott、Suzanne E. Nutter、Wendy H. Gough、Theresa A. Branchek、John M. Zgombick、Sandra A. Filla

  DOI：10.1016/j.bmcl.2003.09.091

  日期：2004.1

  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.