N-(2-cyanophenyl)pyridine-3-carboxamide | 461418-85-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-cyanophenyl)pyridine-3-carboxamide
• CAS: 461418-85-9
• 化学式: C₁₃H₉N₃O
• mdl: MFCD03245930
• 分子量: 223.234
• InChiKey: JZMLNWODSLVDBB-UHFFFAOYSA-N

物化性质

• 沸点：
  335.5±22.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 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：
  65.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-cyanophenyl)pyridine-3-carboxamide 在 五氯化磷 作用下， 以 环丁砜 为溶剂， 反应 10.0h， 以400 mg的产率得到4-氯-2-(3-吡啶基)-喹唑啉
  参考文献：
  名称：

  Convenient and Practical One-Pot Synthesis of 4-Chloropyrimidines via a Novel Chloroimidate Annulation

  摘要：

  Reaction of aromatic or heteroaromatic 2-acyl(amino)nitriles with phosphorus pentachloride triggers a novel chloroimidate cyclization, leading directly to the corresponding annullated 4-chloropyrimidines in good to excellent yields. The reaction lends itself to the telescoped one-pot construction of 4-functionalized pyrimidines from the corresponding (hetero)aromatic 2-aminonitriles. For a pyrazolopyrimidine development intermediate, this reaction was scaled up to multikilogram scale with excellent results. A total of 10 examples with different substrates are provided. This one-pot reaction provides an attractive and sustainable alternative to the commonly used multistep methodology for this transformation.

  DOI：

  10.1021/op1002352
• 作为产物：
  描述：

  氯化烟碱盐酸盐 、 2-氨基苯甲腈 以 环丁砜 为溶剂， 反应 12.0h， 生成 N-(2-cyanophenyl)pyridine-3-carboxamide
  参考文献：
  名称：

  Convenient and Practical One-Pot Synthesis of 4-Chloropyrimidines via a Novel Chloroimidate Annulation

  摘要：

  Reaction of aromatic or heteroaromatic 2-acyl(amino)nitriles with phosphorus pentachloride triggers a novel chloroimidate cyclization, leading directly to the corresponding annullated 4-chloropyrimidines in good to excellent yields. The reaction lends itself to the telescoped one-pot construction of 4-functionalized pyrimidines from the corresponding (hetero)aromatic 2-aminonitriles. For a pyrazolopyrimidine development intermediate, this reaction was scaled up to multikilogram scale with excellent results. A total of 10 examples with different substrates are provided. This one-pot reaction provides an attractive and sustainable alternative to the commonly used multistep methodology for this transformation.

  DOI：

  10.1021/op1002352

文献信息

• ORGANIC COMPOUNDS
  申请人：Adams Christopher

  公开号：US20110082129A1

  公开（公告）日：2011-04-07

  The present invention provides novel organic compounds of Formula I: methods of use, and pharmaceutical compositions thereof.

  本发明提供了化合物I的新型有机化合物，使用方法和其药物组成物。
• US8791141B2
  申请人：——

  公开号：US8791141B2

  公开（公告）日：2014-07-29
• Convenient and Practical One-Pot Synthesis of 4-Chloropyrimidines via a Novel Chloroimidate Annulation
  作者：Thomas Storz、Richard Heid、Joseph Zeldis、Steven M. Hoagland、Vito Rapisardi、Susan Hollywood、George Morton

  DOI：10.1021/op1002352

  日期：2011.7.15

  Reaction of aromatic or heteroaromatic 2-acyl(amino)nitriles with phosphorus pentachloride triggers a novel chloroimidate cyclization, leading directly to the corresponding annullated 4-chloropyrimidines in good to excellent yields. The reaction lends itself to the telescoped one-pot construction of 4-functionalized pyrimidines from the corresponding (hetero)aromatic 2-aminonitriles. For a pyrazolopyrimidine development intermediate, this reaction was scaled up to multikilogram scale with excellent results. A total of 10 examples with different substrates are provided. This one-pot reaction provides an attractive and sustainable alternative to the commonly used multistep methodology for this transformation.