tert-butyl 4-(1,2,4-triazin-3-yl)piperazine-1-carboxylate | 1379522-64-1

• 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: tert-butyl 4-(1,2,4-triazin-3-yl)piperazine-1-carboxylate
• CAS: 1379522-64-1
• 化学式: C₁₂H₁₉N₅O₂
• 分子量: 265.315
• InChiKey: NUPQEXQKBNTFLD-UHFFFAOYSA-N

物化性质

• 沸点：
  415.4±55.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(1,2,4-triazin-3-yl)piperazine-1-carboxylate 在 copper(l) iodide 、 3,4,7,8-四甲基-1,10-菲罗啉 、 溴 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 20.33h， 生成 tert-butyl 4-(6-{[4-(methylsulfonyl)benzyl]oxy}-1,2,4-triazin-3-yl)piperazine-1-carboxylate
  参考文献：
  名称：

  Use of Small-Molecule Crystal Structures To Address Solubility in a Novel Series of G Protein Coupled Receptor 119 Agonists: Optimization of a Lead and in Vivo Evaluation

  摘要：

  G protein coupled receptor 119 (GPR119) is viewed as an attractive target for the treatment of type 2 diabetes and other elements of the metabolic syndrome. During a program toward discovering agonists of GPR119, we herein describe optimization of an initial lead compound, 2, into a development candidate, 42. A key challenge in this program of work was the insolubility of the lead compound. Small-molecule crystallography was utilized to understand the intermolecular interactions in the solid state and resulted in a switch from an aryl sulphone to a 3-cyanopyridyl motif. The compound was shown to be effective in wild-type but not knockout animals, confirming that the biological effects were due to GPR119 agonism.

  DOI：

  10.1021/jm300310c
• 作为产物：
  描述：

  3-甲硫基-1,2,4-三嗪 、 N-Boc-哌嗪 以 乙醇 为溶剂， 反应 24.0h， 以63%的产率得到tert-butyl 4-(1,2,4-triazin-3-yl)piperazine-1-carboxylate
  参考文献：
  名称：

  Use of Small-Molecule Crystal Structures To Address Solubility in a Novel Series of G Protein Coupled Receptor 119 Agonists: Optimization of a Lead and in Vivo Evaluation

  摘要：

  G protein coupled receptor 119 (GPR119) is viewed as an attractive target for the treatment of type 2 diabetes and other elements of the metabolic syndrome. During a program toward discovering agonists of GPR119, we herein describe optimization of an initial lead compound, 2, into a development candidate, 42. A key challenge in this program of work was the insolubility of the lead compound. Small-molecule crystallography was utilized to understand the intermolecular interactions in the solid state and resulted in a switch from an aryl sulphone to a 3-cyanopyridyl motif. The compound was shown to be effective in wild-type but not knockout animals, confirming that the biological effects were due to GPR119 agonism.

  DOI：

  10.1021/jm300310c