1-benzyl-N-butyl-5-methyl-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridine-7-carboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-benzyl-N-butyl-5-methyl-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridine-7-carboxamide
• 英文别名: 1-benzyl-N-butyl-5-methyl-4-oxopyrazolo[4,3-c]pyridine-7-carboxamide
• 化学式: C₁₉H₂₂N₄O₂
• 分子量: 338.409
• InChiKey: PKIGSBFANSNTHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  benzyl 1-benzyl-5-methyl-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridine-7-carboxylate 在 双(五氟苯基)碳酸 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、400.01 kPa 条件下， 反应 27.0h， 生成 1-benzyl-N-butyl-5-methyl-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridine-7-carboxamide
  参考文献：
  名称：

  Synthesis of 1,5-disubstituted-4-oxo-4,5-dihydro-1 H -pyrazolo[4,3- c ]pyridine-7-carboxamides

  摘要：

  1,5-Disubstituted-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridine-7-carboxamides functionalized at positions 1, 5, and 7 were prepared in six straightforward steps from cheap, commercially available dialkyl acetone-1,3-dicarboxylate. Due to the instability of methyl 1-benzyl-substituted pyrazolo[4,3-c]pyridine-7-carboxylates under basic hydrolytic conditions (LiOH/H2O), a detour via the corresponding benzyl esters was introduced to deliver the final 1-benzyl-substituted-bicyclic carboxamides in seven steps. The designed synthetic route is suitable for the construction of a larger library of compounds. All the key compounds have been characterized by NMR spectroscopic techniques and X-ray analysis. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.11.034

文献信息

• Synthesis of 1,5-disubstituted-4-oxo-4,5-dihydro-1 H -pyrazolo[4,3- c ]pyridine-7-carboxamides
  作者：Uroš Grošelj、Eva Pušavec、Amalija Golobič、Georg Dahmann、Branko Stanovnik、Jurij Svete

  DOI：10.1016/j.tet.2014.11.034

  日期：2015.1

  1,5-Disubstituted-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridine-7-carboxamides functionalized at positions 1, 5, and 7 were prepared in six straightforward steps from cheap, commercially available dialkyl acetone-1,3-dicarboxylate. Due to the instability of methyl 1-benzyl-substituted pyrazolo[4,3-c]pyridine-7-carboxylates under basic hydrolytic conditions (LiOH/H2O), a detour via the corresponding benzyl esters was introduced to deliver the final 1-benzyl-substituted-bicyclic carboxamides in seven steps. The designed synthetic route is suitable for the construction of a larger library of compounds. All the key compounds have been characterized by NMR spectroscopic techniques and X-ray analysis. (C) 2014 Elsevier Ltd. All rights reserved.