6-bromo-2-(3,3-dimethoxycyclobutyl)benzothiazole | 1416049-94-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 6-bromo-2-(3,3-dimethoxycyclobutyl)benzothiazole
• 英文别名: 6-Bromo-2-(3,3-dimethoxycyclobutyl)benzothiazole；6-bromo-2-(3,3-dimethoxycyclobutyl)-1,3-benzothiazole
• CAS: 1416049-94-9
• 化学式: C₁₃H₁₄BrNO₂S
• 分子量: 328.23
• InChiKey: ZDLACMQUWJHBSC-UHFFFAOYSA-N

物化性质

• 沸点：
  398.3±42.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-bromo-2-(3,3-dimethoxycyclobutyl)benzothiazole 在 吡啶 、 盐酸 、 sodium tripivaloyloxyborohydride 、 potassium carbonate 、 copper(l) chloride 、 N,N'-二甲基乙二胺 作用下， 以 水 、 甲苯 、 乙腈 为溶剂， 反应 34.0h， 生成 cis-2-[2-(3-piperidin-1-ylcyclobutyl)-1,3-benzothiazol-6-yl]pyridazin-3(2H)-one
  参考文献：
  名称：

  Scalable Synthesis of a Cis-Substituted Cyclobutyl-Benzothiazole Pyridazinone: Process Development of an Efficient Copper Catalyzed C–N Cross-Coupling Reaction

  摘要：

  A scalable process for the preparation of 2-(2-(cis-3-(piperidin-1-yl)cyclobutyl)benzothiazol-6-yl)pyridazin-3(2H)-one in multi-kilogram amounts and in high purity has been developed. The key features of this synthesis are the copper-catalyzed C-N cross-coupling reaction and the development of a highly diastereoselective reductive amination using NaBH(OPiv)(3) as a reducing agent. Controls were implemented to minimize both base- and acid-catalyzed isomerization of the 1,3-cis-substituted cyclobutane ring.

  DOI：

  10.1021/op3002883
• 作为产物：
  描述：

  甲醇 、 3-(6-溴苯并噻唑-2-基)环丁烷酮 以 N-甲基吡咯烷酮 为溶剂， 反应 16.0h， 以112 g的产率得到6-bromo-2-(3,3-dimethoxycyclobutyl)benzothiazole
  参考文献：
  名称：

  Scalable Synthesis of a Cis-Substituted Cyclobutyl-Benzothiazole Pyridazinone: Process Development of an Efficient Copper Catalyzed C–N Cross-Coupling Reaction

  摘要：

  A scalable process for the preparation of 2-(2-(cis-3-(piperidin-1-yl)cyclobutyl)benzothiazol-6-yl)pyridazin-3(2H)-one in multi-kilogram amounts and in high purity has been developed. The key features of this synthesis are the copper-catalyzed C-N cross-coupling reaction and the development of a highly diastereoselective reductive amination using NaBH(OPiv)(3) as a reducing agent. Controls were implemented to minimize both base- and acid-catalyzed isomerization of the 1,3-cis-substituted cyclobutane ring.

  DOI：

  10.1021/op3002883

文献信息

• Scalable Synthesis of a Cis-Substituted Cyclobutyl-Benzothiazole Pyridazinone: Process Development of an Efficient Copper Catalyzed C–N Cross-Coupling Reaction
  作者：Jeffrey M. Kallemeyn、Yi-Yin Ku、Mathew M. Mulhern、Richard Bishop、Agnes Pal、Legi Jacob

  DOI：10.1021/op3002883

  日期：2014.1.17

  A scalable process for the preparation of 2-(2-(cis-3-(piperidin-1-yl)cyclobutyl)benzothiazol-6-yl)pyridazin-3(2H)-one in multi-kilogram amounts and in high purity has been developed. The key features of this synthesis are the copper-catalyzed C-N cross-coupling reaction and the development of a highly diastereoselective reductive amination using NaBH(OPiv)(3) as a reducing agent. Controls were implemented to minimize both base- and acid-catalyzed isomerization of the 1,3-cis-substituted cyclobutane ring.