4-methyl-N-{2-[4-(toluene-4-sulfonyl)-piperazin-1-yl]-ethyl}-benzenesulfonamide | 97257-96-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-methyl-N-{2-[4-(toluene-4-sulfonyl)-piperazin-1-yl]-ethyl}-benzenesulfonamide
• 英文别名: 4-(4-Toluolsulfonyl)-1-<2-(4-toluolsulfamido)ethyl>-piperazin；1-(toluene-4-sulfonyl)-4-[2-(toluene-4-sulfonylamino)-ethyl]-piperazine；4-methyl-N-(2-{4-[(4-methylphenyl)sulfonyl]piperazin-1-yl}ethyl)benzenesulfonamide；4-methyl-N-[2-[4-(4-methylphenyl)sulfonylpiperazin-1-yl]ethyl]benzenesulfonamide
• CAS: 97257-96-0
• 化学式: C₂₀H₂₇N₃O₄S₂
• mdl: MFCD03403551
• 分子量: 437.584
• InChiKey: ZYVWZVBUZKKDEZ-UHFFFAOYSA-N

物化性质

• 熔点：
  149 °C
• 沸点：
  607.7±65.0 °C(Predicted)
• 密度：
  1.283±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N,N-双-2-氯乙基对甲苯磺酸胺 、 (R)-1-(4-氟苯基)乙胺 在 N,N-二异丙基乙胺 作用下， 反应 36.0h， 以96%的产率得到(R)-1-(1-(4-fluorophenyl)ethyl)-4-tosylpiperazine
  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.