2-chloro-N-cyclopentyl-5-(3,3-diethoxypropyl-1-yn-1-yl)pyrimidin-4-amine | 1211442-87-3

• 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: 2-chloro-N-cyclopentyl-5-(3,3-diethoxypropyl-1-yn-1-yl)pyrimidin-4-amine
• 英文别名: [2-chloro-5-(3,3-diethoxy-prop-1-ynyl)-pyrimidin-4-yl]-cyclopentyl amine；[2-Chloro-5-(3,3-diethoxy-prop-1-ynyl)-pyrimidin-4-yl]cyclopentylamine；2-chloro-N-cyclopentyl-5-(3,3-diethoxyprop-1-ynyl)pyrimidin-4-amine
• CAS: 1211442-87-3
• 化学式: C₁₆H₂₂ClN₃O₂
• 分子量: 323.823
• InChiKey: NPWHRGNZZPOQJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  56.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-chloro-N-cyclopentyl-5-(3,3-diethoxypropyl-1-yn-1-yl)pyrimidin-4-amine 在 盐酸 、 甲醇 、 四丁基氟化铵 、 水 、 palladium diacetate 、 caesium carbonate 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 potassium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 生成 7-cyclopentyl-2-((1-methyl-5-(4-methylpiperazine-1-carbonyl)-1H-pyrrol-3-yl)amino)-7H-pyrrolo[2,3-d]pyrimidine-6-carbaldehyde
  参考文献：
  名称：

  Structure-based design of 2,6,7-trisubstituted-7H-pyrrolo[2,3-d]pyrimidines as Aurora kinases inhibitors

  摘要：

  This Letter reports the optimization of a pyrrolopyrimidine series as dual inhibitors of Aurora A/B kinases. This series derived from a pyrazolopyrimidine series previously reported as inhibitors of aurora kinases and CDKs. In an effort to improve the selectivity of this chemotype, we switched to the pyrrolopyrimidine core which allowed functionalization on C-2. In addition, the modeling rationale was based on superimposing the structures of Aurora-A kinase and CDK2 which revealed enough differences leading to a path for selectivity improvement. The synthesis of the new series of pyrrolopyrimidine analogs relied on the development of a different route for the two key intermediates 7 and 19 which led to analogs with both tunable activity against CDK1 and maintained cell potency. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.085
• 作为产物：
  描述：

  环戊胺 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-chloro-N-cyclopentyl-5-(3,3-diethoxypropyl-1-yn-1-yl)pyrimidin-4-amine
  参考文献：
  名称：

  Structure-based design of 2,6,7-trisubstituted-7H-pyrrolo[2,3-d]pyrimidines as Aurora kinases inhibitors

  摘要：

  This Letter reports the optimization of a pyrrolopyrimidine series as dual inhibitors of Aurora A/B kinases. This series derived from a pyrazolopyrimidine series previously reported as inhibitors of aurora kinases and CDKs. In an effort to improve the selectivity of this chemotype, we switched to the pyrrolopyrimidine core which allowed functionalization on C-2. In addition, the modeling rationale was based on superimposing the structures of Aurora-A kinase and CDK2 which revealed enough differences leading to a path for selectivity improvement. The synthesis of the new series of pyrrolopyrimidine analogs relied on the development of a different route for the two key intermediates 7 and 19 which led to analogs with both tunable activity against CDK1 and maintained cell potency. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.085

文献信息

• [EN] PYRROLOPYRIMIDINE COMPOUNDS AS CDK INHIBITORS<br/>[FR] COMPOSÉS DE PYRROLOPYRIMIDINE ET LEURS UTILISATIONS
  申请人：NOVARTIS AG

  公开号：WO2010020675A1

  公开（公告）日：2010-02-25

  The disclosed compounds relate to treatments and therapies for protein kinase-associated disorders. There is also a need for compounds useful in the treatment or prevention or amelioration of one or more symptoms of cancer, transplant rejections, and autoimmune diseases. Furthermore, there is a need for methods for modulating the activity of protein kinases, such as CDK1, CDK2, CDK4, CDK5, CDK6, CDK7, CDK8 and CDK9, using the compounds provided herein.

  所披露的化合物涉及治疗与蛋白激酶相关的疾病。此外，还需要用于治疗、预防或改善癌症、移植排斥和自身免疫疾病的一个或多个症状的化合物。更进一步，还需要使用本处提供的化合物来调节蛋白激酶活性的方法，如CDK1、CDK2、CDK4、CDK5、CDK6、CDK7、CDK8和CDK9。
• Processes for the Preparation of Ribociclib and Intermediates Thereof
  申请人：Apotex Inc.

  公开号：US20190345163A1

  公开（公告）日：2019-11-14

  The present invention provides processes for the preparation of Ribociclib, as well as intermediates useful in the preparation thereof. In particular, processes are provided for the preparation of a compound of Formula (4), and its conversion to Ribociclib (1).

  本发明提供了制备Ribociclib的工艺，以及在制备过程中有用的中间体。具体而言，提供了制备化合物Formula（4）及其转化为Ribociclib（1）的工艺。
• PYRROLOPYRIMIDINE COMPOUNDS AND THEIR USES
  申请人：NOVARTIS AG

  公开号：US20130184285A1

  公开（公告）日：2013-07-18

  The disclosed compounds relate to treatments and therapies for protein kinase-associated disorders. There is also a need for compounds useful in the treatment or prevention or amelioration of one or more symptoms of cancer, transplant rejections, and autoimmune diseases. Furthermore, there is a need for methods for modulating the activity of protein kinases, such as CDK1, CDK2, CDK4, CDK5, CDK6, CDK7, CDK8 and CDK9, using the compounds provided herein.

  所透露的化合物涉及蛋白激酶相关疾病的治疗和疗法。还需要用于治疗、预防或改善癌症、移植排斥和自身免疫性疾病一种或多种症状的化合物。此外，还需要使用此处提供的化合物调节蛋白激酶活性的方法，如CDK1、CDK2、CDK4、CDK5、CDK6、CDK7、CDK8和CDK9。
• Processes for the preparation of Ribociclib and intermediates thereof
  申请人：Apotex Inc.

  公开号：US10723739B2

  公开（公告）日：2020-07-28

  The present invention provides processes for the preparation of Ribociclib, as well as intermediates useful in the preparation thereof. In particular, processes are provided for the preparation of a compound of Formula (4), and its conversion to Ribociclib (1).

  本发明提供了制备Ribociclib的方法，以及在其制备过程中有用的中间体。具体而言，提供了制备化合物式（4）的方法及其转化为Ribociclib（1）的方法。
• Pyrrolopyrimidine compounds and their uses
  申请人：Besong Gilbert Ebai

  公开号：US08685980B2

  公开（公告）日：2014-04-01

  The disclosed compounds relate to treatments and therapies for protein kinase-associated disorders. There is also a need for compounds useful in the treatment or prevention or amelioration of one or more symptoms of cancer, transplant rejections, and autoimmune diseases. Furthermore, there is a need for methods for modulating the activity of protein kinases, such as CDK1, CDK2, CDK4, CDK5, CDK6, CDK7, CDK8 and CDK9, using the compounds provided herein.

  所披露的化合物与蛋白激酶相关的疾病的治疗和疗法有关。还需要用于治疗、预防或改善癌症、移植排斥和自身免疫性疾病的化合物。此外，还需要使用此处提供的化合物调节蛋白激酶活性的方法，如CDK1、CDK2、CDK4、CDK5、CDK6、CDK7、CDK8和CDK9。