N-(3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl)acetamide | 1224289-08-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N-(3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl)acetamide
• CAS: 1224289-08-0
• 化学式: C₁₅H₁₁N₅O
• 分子量: 277.285
• InChiKey: ZULNWVSKWUAHLL-UHFFFAOYSA-N

物化性质

• 熔点：
  255-256 °C(Solv: acetic acid (64-19-7))
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.23
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  83.08
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-(3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl)acetamide 、 碘乙烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 以55.7%的产率得到N-(3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl)-N-ethylacetamide
  参考文献：
  名称：

  Synthetic Studies Connected with the Preparation of N-[3-(3-Cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl]-N-ethylacetamide, a Zaleplon Regioisomer

  摘要：

  N-[3-(3-Cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl]-N-ethyl-acetamide, a principal impurity of zaleplon, is prepared by Suzuki-Miyaura cross coupling reaction of the corresponding boronic acid and/or boronates with 5-chloropyrazolo[1,5-a]pyrimidin-3-carbonitrile (7). Various methods of preparation of both components are described, as well as approaches based on the final modification of the 5-(3-aminophenyl)-pyrazolo[1,5-a]pyrimidine-3-carbonitrile moiety prepared by Suzuki-Miyaura cross coupling. All the prepared compounds were unambiguouesly identified by NMR techniques. Spectral characteristics (IR, UV, MS) of these compounds are also given.

  DOI：

  10.3987/com-09-s(s)129
• 作为产物：
  描述：

  5-氯吡唑并[1,5-a]嘧啶-3-甲腈 、 3-乙酰胺基苯硼酸 在 trisodium tris(3-sulfophenyl)phosphine 、 palladium diacetate 、 caesium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以93.8%的产率得到N-(3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl)acetamide
  参考文献：
  名称：

  Synthetic Studies Connected with the Preparation of N-[3-(3-Cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl]-N-ethylacetamide, a Zaleplon Regioisomer

  摘要：

  N-[3-(3-Cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl]-N-ethyl-acetamide, a principal impurity of zaleplon, is prepared by Suzuki-Miyaura cross coupling reaction of the corresponding boronic acid and/or boronates with 5-chloropyrazolo[1,5-a]pyrimidin-3-carbonitrile (7). Various methods of preparation of both components are described, as well as approaches based on the final modification of the 5-(3-aminophenyl)-pyrazolo[1,5-a]pyrimidine-3-carbonitrile moiety prepared by Suzuki-Miyaura cross coupling. All the prepared compounds were unambiguouesly identified by NMR techniques. Spectral characteristics (IR, UV, MS) of these compounds are also given.

  DOI：

  10.3987/com-09-s(s)129