2-Chloro-N-(2'-chloro-5'-pyridinyl)pyridine-3-carboxamide | 152038-51-2

• 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: 2-Chloro-N-(2'-chloro-5'-pyridinyl)pyridine-3-carboxamide
• 英文别名: 2-Chloro-N-(6-chloropyridin-3-yl)pyridine-3-carboxamide
• CAS: 152038-51-2
• 化学式: C₁₁H₇Cl₂N₃O
• 分子量: 268.102
• InChiKey: KLBOLVOJHSLGII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Chloro-N-(2'-chloro-5'-pyridinyl)pyridine-3-carboxamide 在 sodium hexamethyldisilazane 、 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二甲基亚砜 、 xylene 为溶剂， 反应 5.08h， 生成 2--N-methylpyridine-3-carboxamide
  参考文献：
  名称：

  A novel Smiles rearrangement gives access to the A-ring pyridine isomers of the nevirapine ring system

  摘要：

  The cyclization of N-methylamide 9 gives, along with the expected product 2, the isomeric diazepinone 3 resulting.from a novel Smiles rearrangement in which an N-methylcarboxamide functions as a leaving group. The mechanism of the reaction has been proven by isolation of the intermediate 10 and by conducting the rearrangement on the model compound 13. The relative amounts of 2, 3, and 10 formed from 9 are subject to some control by variation of the base and reaction temperature (Table I). This new Smiles rearrangement was applied to the synthesis of the remaining two A-ring isomers 4 and 5 of the nevirapine ring system 1 by cyclization of the thioether 16 and the sulfoxide 17.

  DOI：

  10.1021/jo00077a016
• 作为产物：
  描述：

  2-氯-5-氨基吡啶 、 2-氯烟酰氯 以 氯仿 、 乙酸乙酯 为溶剂， 以99%的产率得到2-Chloro-N-(2'-chloro-5'-pyridinyl)pyridine-3-carboxamide
  参考文献：
  名称：

  A novel Smiles rearrangement gives access to the A-ring pyridine isomers of the nevirapine ring system

  摘要：

  The cyclization of N-methylamide 9 gives, along with the expected product 2, the isomeric diazepinone 3 resulting.from a novel Smiles rearrangement in which an N-methylcarboxamide functions as a leaving group. The mechanism of the reaction has been proven by isolation of the intermediate 10 and by conducting the rearrangement on the model compound 13. The relative amounts of 2, 3, and 10 formed from 9 are subject to some control by variation of the base and reaction temperature (Table I). This new Smiles rearrangement was applied to the synthesis of the remaining two A-ring isomers 4 and 5 of the nevirapine ring system 1 by cyclization of the thioether 16 and the sulfoxide 17.

  DOI：

  10.1021/jo00077a016

文献信息

• A novel Smiles rearrangement gives access to the A-ring pyridine isomers of the nevirapine ring system
  作者：John R. Proudfoot、Usha R. Patel、Scot J. Campbell

  DOI：10.1021/jo00077a016

  日期：1993.12

  The cyclization of N-methylamide 9 gives, along with the expected product 2, the isomeric diazepinone 3 resulting.from a novel Smiles rearrangement in which an N-methylcarboxamide functions as a leaving group. The mechanism of the reaction has been proven by isolation of the intermediate 10 and by conducting the rearrangement on the model compound 13. The relative amounts of 2, 3, and 10 formed from 9 are subject to some control by variation of the base and reaction temperature (Table I). This new Smiles rearrangement was applied to the synthesis of the remaining two A-ring isomers 4 and 5 of the nevirapine ring system 1 by cyclization of the thioether 16 and the sulfoxide 17.