tert-butyl (S)-2-((2-(6-chloropyrimidin-4-yl)-5-(trifluoromethyl)phenyl)carbamoyl)pyrrolidine-1-carboxylate | 1078132-72-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (S)-2-((2-(6-chloropyrimidin-4-yl)-5-(trifluoromethyl)phenyl)carbamoyl)pyrrolidine-1-carboxylate
• CAS: 1078132-72-5
• 化学式: C₂₁H₂₂ClF₃N₄O₃
• 分子量: 470.879
• InChiKey: LWIKVYNQCFRSIQ-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.15
• 重原子数：
  32.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  84.42
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-2-((2-(6-chloropyrimidin-4-yl)-5-(trifluoromethyl)phenyl)carbamoyl)pyrrolidine-1-carboxylate 、 N-(4-羟基-2-苯并噻唑基)-乙酰胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以79%的产率得到(2S)-tert-butyl 2-((2-(6-(2-acetamidobenzo[d]thiazol-4-yloxy)pyrimidin-4-yl)-5-(trifluoromethyl)phenyl)carbamoyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Substituted aryl pyrimidines as potent and soluble TRPV1 antagonists

  摘要：

  Clinical candidate AMG 517 (1) is a potent antagonist toward multiple modes of activation of TRPV1; however, it suffers from poor solubility. Analogs with various substituents at the R region of 3 were prepared to improve the solubility while maintaining the potent TRPV1 activity of 1. Compounds were identified that maintained potency, had good pharmacokinetic properties, and improved solubility relative to 1. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.07.112
• 作为产物：
  描述：

  2-(6-chloropyrimidin-4-yl)-5-(trifluoromethyl)benzeneamine 、 BOC-L-脯氨酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到tert-butyl (S)-2-((2-(6-chloropyrimidin-4-yl)-5-(trifluoromethyl)phenyl)carbamoyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Substituted aryl pyrimidines as potent and soluble TRPV1 antagonists

  摘要：

  Clinical candidate AMG 517 (1) is a potent antagonist toward multiple modes of activation of TRPV1; however, it suffers from poor solubility. Analogs with various substituents at the R region of 3 were prepared to improve the solubility while maintaining the potent TRPV1 activity of 1. Compounds were identified that maintained potency, had good pharmacokinetic properties, and improved solubility relative to 1. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.07.112