2-(2-(3,3-dimethoxycyclobutyl)benzothiazol-6-yl)-pyridazin-3(2H)-one | 1416049-95-0

• 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: 2-(2-(3,3-dimethoxycyclobutyl)benzothiazol-6-yl)-pyridazin-3(2H)-one
• 英文别名: 2-[2-(3,3-Dimethoxycyclobutyl)-1,3-benzothiazol-6-yl]pyridazin-3-one
• CAS: 1416049-95-0
• 化学式: C₁₇H₁₇N₃O₃S
• 分子量: 343.406
• InChiKey: IZMVWBZWMLHNHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  92.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(2-(3,3-dimethoxycyclobutyl)benzothiazol-6-yl)-pyridazin-3(2H)-one 在 盐酸 、 sodium cyanoborohydride 作用下， 以 甲醇 、 乙醇 、 水 、 甲苯 、 乙腈 为溶剂， 反应 31.5h， 生成 2-(2-(cis-3-(piperidin-1-yl)cyclobutyl)benzothiazol-6-yl)pyridazin-3(2H)-one hydrochloride
  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：

  3-哒嗪酮 、 6-bromo-2-(3,3-dimethoxycyclobutyl)benzothiazole 在 吡啶 、 potassium carbonate 、 copper(l) chloride 、 N,N'-二甲基乙二胺 作用下， 反应 16.5h， 以84%的产率得到2-(2-(3,3-dimethoxycyclobutyl)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