4,6-bis-{4-[(R)-1-(4-fluoro-phenyl)-ethyl]-piperazin-1-yl}-pyrimidine | 1020064-28-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4,6-bis-{4-[(R)-1-(4-fluoro-phenyl)-ethyl]-piperazin-1-yl}-pyrimidine
• 英文别名: 4,6-bis[4-[(1R)-1-(4-fluorophenyl)ethyl]piperazin-1-yl]pyrimidine
• CAS: 1020064-28-1
• 化学式: C₂₈H₃₄F₂N₆
• 分子量: 492.615
• InChiKey: IEOSFSQGBIRKOL-FGZHOGPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (R)-1-(1-(4-氟苯基)乙基)哌嗪 、 4,6-二氯嘧啶 以 二甲基亚砜 为溶剂， 生成 4-chloro-6-{4-[(R)-1-(4-fluoro-phenyl)-ethyl]-piperazin-1-yl}-pyrimidine 、 4,6-bis-{4-[(R)-1-(4-fluoro-phenyl)-ethyl]-piperazin-1-yl}-pyrimidine
  参考文献：
  名称：

  Practical Synthesis of a Vanilloid Receptor-1 Antagonist

  摘要：

  Small molecule TRPV1 antagonists have been a recent focus in the search for pain treatment agents. We herein describe a practical and scalable synthesis of AMG 628 (1), a bis-substituted pyrimidine derivative that was identified as a highly efficacious agent, suitable for clinical development. Highlights of our approach include a practical route to a substituted benzothiazole, a scalable synthesis of an enantiopure piperazine fragment, and identification of conditions for selective coupling reactions on 2,6-dichloropyrimidine, to access the active pharmaceutical ingredient in high purity and overall yield.

  DOI：

  10.1021/jo8002216

文献信息

• Practical Synthesis of a Vanilloid Receptor-1 Antagonist
  作者：Oliver R. Thiel、Charles Bernard、Tony King、Mina Dilmeghani-Seran、Tracy Bostick、Robert D. Larsen、Margaret M. Faul

  DOI：10.1021/jo8002216

  日期：2008.5.1

  Small molecule TRPV1 antagonists have been a recent focus in the search for pain treatment agents. We herein describe a practical and scalable synthesis of AMG 628 (1), a bis-substituted pyrimidine derivative that was identified as a highly efficacious agent, suitable for clinical development. Highlights of our approach include a practical route to a substituted benzothiazole, a scalable synthesis of an enantiopure piperazine fragment, and identification of conditions for selective coupling reactions on 2,6-dichloropyrimidine, to access the active pharmaceutical ingredient in high purity and overall yield.