6-(tert-butoxycarbonyl(methyl)amino)benzo[d]thiazole | 1219133-04-6

• 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-(tert-butoxycarbonyl(methyl)amino)benzo[d]thiazole
• 英文别名: 6-t-butoxycarbonylmethylaminobenzothiazole；tert-butyl N-(1,3-benzothiazol-6-yl)-N-methylcarbamate
• CAS: 1219133-04-6
• 化学式: C₁₃H₁₆N₂O₂S
• 分子量: 264.348
• InChiKey: DOVANUAJKWMIEX-UHFFFAOYSA-N

物化性质

• 沸点：
  369.8±15.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  70.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(tert-butoxycarbonyl(methyl)amino)benzo[d]thiazole 、 N-chloro-N-sodio-tert-butylcarbamate 在 [Cu(1,3-di-iso-propylimidazolin-2-ylidene)(Cl)] 、 sodium t-butanolate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以75%的产率得到2-tert-butoxycarbonylamino-6-(tert-butoxycarbonyl(methyl)amino)benzo[d]thiazole
  参考文献：
  名称：

  (NHC)Cu 催化的（杂）芳烃与可脱保护氨基甲酸酯的轻度 C-H 酰胺化：范围和机理研究

  摘要：

  芳基伯胺是合成、生物和材料科学中广泛存在的重要单元。在本文中，我们描述了 (NHC)Cu 系统的开发，该系统通过使用 N-氯代氨基甲酸酯或其钠衍生物作为实用的氨基源来介导（杂）芳烃的直接 CH 酰胺化。反应性铜-芳基中间体与酰胺化试剂的轻松化学计量反应使我们分离出关键的芳基氨基甲酸铜物种并形成 CN 键。(t)BuONa 碱的使用使这种转化在温和条件下具有催化作用。目前的 (NHC)Cu 催化的 CH 酰胺化在包括多氟苯、唑类和喹啉 N-氧化物在内的一系列芳烃上高效且选择性地大规模工作。

  DOI：

  10.1021/jacs.6b07486
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 N-甲基-6-苯并噻唑胺 在 zinc perchlorate 作用下， 以 叔丁醇 为溶剂， 反应 3.0h， 以72%的产率得到6-(tert-butoxycarbonyl(methyl)amino)benzo[d]thiazole
  参考文献：
  名称：

  Synthesis and Evaluation of Three ¹⁸F-Labeled Aminophenylbenzothiazoles as Amyloid Imaging Agents

  摘要：

  We have developed three fluorine-18 labeled 6-(methyl)amino-2-(4'-fluorophenyl)-1,3-benzothiazoles, which display high in vitro binding affinity For human amyloid beta plaques (K-i <= 10 nM). The radiolabeled F, robes were synthesized by aromatic nucleophilic Substitution of the corresponding nitro precursor with F-18-fluoride, followed by deprotection of the BOC group if required. Determination of the octanol/water partition coefficient, biodistribution studies In mice, and in vivo mu PET studies in rats and a rhesus monkey showed that initial brain uptake was high and brain washout was fast in normal animals. Radiometabolites were quantified in plasma and brain of mice and in monkey plasma using HPLC. Of the tested compounds, [F-18]2 (6-amino-2-(4'-[F-18]fluorophenyl)-1,3-benzothiazole) shows the most favorable brain kinetics in mice, rats, and a monkey. Its polar plasma radiometabolites do not cross the blood-brain barrier. The preliminary results strongly suggest that this new fluorinated compound is a promising candidate as a PET brain amyloid imaging agent.

  DOI：

  10.1021/jm900871v

文献信息

• NOVEL 3,5-DISUBSTITUTED-3H-IMIDAZO[4,5-B]PYRIDINE AND 3,5- DISUBSTITUTED -3H-[1,2,3]TRIAZOLO[4,5-B] PYRIDINE COMPOUNDS AS MODULATORS OF C-MET PROTEIN, ETC
  申请人：Rhizen Pharmaceuticals SA

  公开号：US20150057309A1

  公开（公告）日：2015-02-26

  The present invention provides compounds useful as c-Met protein kinase modulators, methods of preparing them, pharmaceutical compositions containing them and methods of treatment, prevention and/or amelioration of c-Met kinase mediated disease or disorders with them.

  本发明提供了作为c-Met蛋白激酶调节剂有用的化合物，以及制备它们的方法，含有它们的药物组合物，以及使用它们进行治疗、预防和/或改善c-Met激酶介导的疾病或疾病的方法。
• 3,5-disubstituted-3H-imidazo[4,5-b]pyridine and 3,5-disubstituted-3H-[1,2,3]triazolo[4,5-B] pyridine compounds as modulators of c-Met protein kinases
  申请人：Rhizen Pharmaceuticals SA

  公开号：US11066402B2

  公开（公告）日：2021-07-20

  The present invention provides compounds useful as c-Met protein kinase modulators, methods of preparing them, pharmaceutical compositions containing them and methods of treatment, prevention and/or amelioration of c-Met kinase mediated disease or disorders with them.

  本发明提供了可用作 c-Met 蛋白激酶调节剂的化合物、制备它们的方法、含有它们的药物组合物以及用它们治疗、预防和/或改善 c-Met 激酶介导的疾病或紊乱的方法。
• NOVEL 3,5-DISUBSTITUED-3H-IMIDAZO[4,5-B]PYRIDINE AND 3,5- DISUBSTITUED -3H-[1,2,3]TRIAZOLO[4,5-B]PYRIDINE COMPOUNDS AS MODULATORS OF C-MET PROTEIN KINASES
  申请人：Rhizen Pharmaceuticals S.A.

  公开号：EP2831073B1

  公开（公告）日：2020-12-09
• NOVEL 3,5-DISUBSTITUTED-3H-IMIDAZO[4,5-B]PYRIDINE AND 3,5-DISUBSTITUTED-3H-[1,2,3]TRIAZOLO[4,5-B] PYRIDINE COMPOUNDS AS MODULATORS OF C-MET PROTEIN KINASES
  申请人：Rhizen Pharmaceuticals SA

  公开号：US20180072721A1

  公开（公告）日：2018-03-15

  The present invention provides compounds useful as c-Met protein kinase modulators, methods of preparing them, pharmaceutical compositions containing them and methods of treatment, prevention and/or amelioration of c-Met kinase mediated disease or disorders with them.
• NOVEL 3,5-DISUBSTITUTED-3H-IMIDAZO[4,5-B]PYRIDINE AND 3,5- DISUBSTITUTED -3H-[1,2,3]TRIAZOLO[4,5-B] PYRIDINE COMPOUNDS AS MODULATORS OF C-MET PROTEIN KINASES
  申请人：Rhizen Pharmaceuticals SA

  公开号：US20210371416A1

  公开（公告）日：2021-12-02

  The present invention provides compounds useful as c-Met protein kinase modulators, methods of preparing them, pharmaceutical compositions containing them and methods of treatment, prevention and/or amelioration of c-Met kinase mediated disease or disorders with them.