2-(2-(3-oxocyclobutyl)benzothiazol-6-yl)pyridazin-3(2H)-one | 929608-15-1

• 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-oxocyclobutyl)benzothiazol-6-yl)pyridazin-3(2H)-one
• 英文别名: 2-[2-(3-oxo-cyclobutyl)-1,3-benzothiazol-6-yl]-2H-pyridazin-3-one；2-[2-(3-oxocyclobutyl)-1,3-benzothiazol-6-yl]pyridazin-3-one
• CAS: 929608-15-1
• 化学式: C₁₅H₁₁N₃O₂S
• 分子量: 297.337
• InChiKey: KCYBHHLXWJWORQ-UHFFFAOYSA-N

物化性质

• 熔点：
  >200 °C
• 沸点：
  524.0±60.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  90.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-(3-oxocyclobutyl)benzothiazol-6-yl)pyridazin-3(2H)-one 在 盐酸 、 sodium cyanoborohydride 作用下， 以 甲醇 、 乙醇 、 甲苯 为溶剂， 反应 30.0h， 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：

  6-bromo-2-(3,3-dimethoxycyclobutyl)benzothiazole 在 吡啶 、 盐酸 、 potassium trimethylsilonate 、 copper(l) chloride 作用下， 以 水 、 乙腈 为溶剂， 反应 23.5h， 生成 2-(2-(3-oxocyclobutyl)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

文献信息

• Benzothiazole cyclobutyl amine derivatives
  申请人：Cowart D. Marlon

  公开号：US20070066588A1

  公开（公告）日：2007-03-22

  Compounds of formula (I) are useful in treating conditions or disorders prevented by or ameliorated by histamine-3 receptor ligands. Also disclosed are pharmaceutical compositions comprising the histamine-3 receptor ligands, methods for using such compounds and compositions, and a process for preparing compounds within the scope of formula (I).

  公式（I）的化合物在治疗由组胺-3受体配体预防或改善的疾病或疾病中是有用的。还公开了包含组胺-3受体配体的药物组合物，使用这类化合物和组合物的方法，以及制备公式（I）范围内化合物的过程。
• BENZOTHIAZOLE CYCLOBUTYL AMINE DERIVATIVES
  申请人：Cowart Marlon D.

  公开号：US20090326222A1

  公开（公告）日：2009-12-31

  Compounds of formula (I) are useful in treating conditions or disorders prevented by or ameliorated by histamine-3 receptor ligands. Also disclosed are pharmaceutical compositions comprising the histamine-3 receptor ligands, methods for using such compounds and compositions, and a process for preparing compounds within the scope of formula (I).

  公式（I）的化合物在治疗由组胺-3受体配体预防或改善的疾病或疾病方面非常有用。还公开了包含组胺-3受体配体的药物组合物，使用此类化合物和组合物的方法以及制备公式（I）范围内化合物的过程。
• Benzothiazole cyclobutyl amine derivatives and their use as histamine-3 receptors ligands
  申请人：Abbott Laboratories

  公开号：EP2386556A1

  公开（公告）日：2011-11-16

  Compounds of formula (I) are useful in treating conditions or disorders prevented by or ameliorated by histamine-3 receptor ligands. Also disclosed are pharmaceutical compositions comprising the histamine-3 receptor ligands, methods for using such compounds and compositions, and a process for preparing compounds within the scope of formula (I).

  式（I）化合物可用于治疗组胺-3 受体配体所预防或改善的病症或紊乱。还公开了包含组胺-3 受体配体的药物组合物、使用此类化合物和组合物的方法以及制备式（I）范围内化合物的工艺。
• BENZOTHIAZOLE CYCLOBUTYL AMINE DERIVATIVES AND THEIR USE AS HISTAMINE-3 RECEPTORS LIGANDS
  申请人：ABBOTT LABORATORIES

  公开号：EP1926729B1

  公开（公告）日：2011-12-21
• US7576110B2
  申请人：——

  公开号：US7576110B2

  公开（公告）日：2009-08-18