N-tert-butyl-8-chlorophthalazine-5-carboxamide | 1100330-17-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N-tert-butyl-8-chlorophthalazine-5-carboxamide
• CAS: 1100330-17-3
• 化学式: C₁₃H₁₄ClN₃O
• 分子量: 263.727
• InChiKey: KLHHSNIFSWGOQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-tert-butyl-5-chloro-3-hydroxy-1-oxoisoindoline-4-carbaldehyde 在 一水合肼 、 溶剂黄146 作用下， 反应 0.5h， 生成 N-tert-butyl-8-chlorophthalazine-5-carboxamide
  参考文献：
  名称：

  Practical Synthesis of a p38 MAP Kinase Inhibitor

  摘要：

  p38 MAP kinase inhibitors have attracted considerable interest as potential agents for the treatment of inflammatory diseases. Herein, we describe a concise and efficient synthesis of inhibitor 1 that is based on a phthalazine scaffold. Highlights of our approach include a practical synthesis of a 1,6-disubstituted phthalazine building block 24 as well as the one-pot formation of boronic acid 27. Significant synthetic work to understand the reactivity principles of the intermediates helped in selection of the final synthetic route. Subsequent optimization of the individual steps of the final sequence led to a practical synthesis of 1.

  DOI：

  10.1021/jo802186m

文献信息

• Practical Synthesis of a p38 MAP Kinase Inhibitor
  作者：Michał Achmatowicz、Oliver R. Thiel、Philip Wheeler、Charles Bernard、Jinkun Huang、Robert D. Larsen、Margaret M. Faul

  DOI：10.1021/jo802186m

  日期：2009.1.16

  p38 MAP kinase inhibitors have attracted considerable interest as potential agents for the treatment of inflammatory diseases. Herein, we describe a concise and efficient synthesis of inhibitor 1 that is based on a phthalazine scaffold. Highlights of our approach include a practical synthesis of a 1,6-disubstituted phthalazine building block 24 as well as the one-pot formation of boronic acid 27. Significant synthetic work to understand the reactivity principles of the intermediates helped in selection of the final synthetic route. Subsequent optimization of the individual steps of the final sequence led to a practical synthesis of 1.