3-[acetyl-(3,5-dimethylphenyl)-amino]-1-(2'-cyanobiphenyl-4-ylmethyl)-1H-pyrazole-4-carboxylic acid ethyl ester | 1335105-24-2

• 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: 3-[acetyl-(3,5-dimethylphenyl)-amino]-1-(2'-cyanobiphenyl-4-ylmethyl)-1H-pyrazole-4-carboxylic acid ethyl ester
• CAS: 1335105-24-2
• 化学式: C₃₀H₂₈N₄O₃
• 分子量: 492.577
• InChiKey: XPERHDQNJIPEFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.95
• 重原子数：
  37.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  88.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-[acetyl-(3,5-dimethylphenyl)-amino]-1-(2'-cyanobiphenyl-4-ylmethyl)-1H-pyrazole-4-carboxylic acid ethyl ester 在 叠氮基三甲基硅烷 、 二正丁基氧化锡 作用下， 以 甲苯 为溶剂， 反应 60.0h， 以74%的产率得到3-[acetyl-(3,5-dimethylphenyl)-amino]-1-[2'-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-1H-pyrazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Application of Ullmann and Ullmann–Finkelstein reactions for the synthesis of N-aryl-N-(1H-pyrazol-3-yl) acetamide or N-(1-aryl-1H-pyrazol-3-yl) acetamide derivatives and pharmacological evaluation

  摘要：

  Ullmann-type reactions are becoming a major tool in medicinal chemistry. In this article, we describe the use of these Copper-catalyzed reactions with various precursors, acyl-heteroarylamines or pyrazoles of interest for pharmacomodulation. To the medicinal chemist they offer new, usually untapped disconnection approaches to compounds of interest. They thus open the way to new original analogues of bioactive compounds possibly not patented, from common building-blocks. They also allow C to N bioisosteric replacements, which sometimes are synthetically challenging. We report for the first time the critical effect of acetylamino substituents on the regioselective arylation of unsymmetrical pyrazoles that are useful for medicinal chemists. Finally, we have applied this strategy to the design of novel AT, receptor antagonists. Though this family has been extensively investigated in the past 30 years, N-arylation and C to N replacement made possible by Ullmann chemistry, can produce original antagonists. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.056
• 作为产物：
  描述：

  3-氨基-4-乙氧羰基吡唑 在 trans-N,N'-dimethyl-1,2-cyclohexyldiamine 、 potassium phosphate 、 copper(l) iodide 、 sodium hydride 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.17h， 生成 3-[acetyl-(3,5-dimethylphenyl)-amino]-1-(2'-cyanobiphenyl-4-ylmethyl)-1H-pyrazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Application of Ullmann and Ullmann–Finkelstein reactions for the synthesis of N-aryl-N-(1H-pyrazol-3-yl) acetamide or N-(1-aryl-1H-pyrazol-3-yl) acetamide derivatives and pharmacological evaluation

  摘要：

  Ullmann-type reactions are becoming a major tool in medicinal chemistry. In this article, we describe the use of these Copper-catalyzed reactions with various precursors, acyl-heteroarylamines or pyrazoles of interest for pharmacomodulation. To the medicinal chemist they offer new, usually untapped disconnection approaches to compounds of interest. They thus open the way to new original analogues of bioactive compounds possibly not patented, from common building-blocks. They also allow C to N bioisosteric replacements, which sometimes are synthetically challenging. We report for the first time the critical effect of acetylamino substituents on the regioselective arylation of unsymmetrical pyrazoles that are useful for medicinal chemists. Finally, we have applied this strategy to the design of novel AT, receptor antagonists. Though this family has been extensively investigated in the past 30 years, N-arylation and C to N replacement made possible by Ullmann chemistry, can produce original antagonists. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.056