5-bromo-3-(phenylethynyl)pyrazin-2-amine | 1349151-88-7

• 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: 5-bromo-3-(phenylethynyl)pyrazin-2-amine
• 英文别名: 5-bromo-3-(2-phenylethynyl)pyrazin-2-amine
• CAS: 1349151-88-7
• 化学式: C₁₂H₈BrN₃
• 分子量: 274.12
• InChiKey: BJAMXDIRSPZEAY-UHFFFAOYSA-N

物化性质

• 沸点：
  428.1±45.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-3-(phenylethynyl)pyrazin-2-amine 在 2-双环己基膦-2',6'-二甲氧基联苯 、 三乙基硅烷 、 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 21.0h， 生成 2-苯基-4,7-二氮杂吲哚
  参考文献：
  名称：

  An efficient one-pot synthesis of 2-bromo-6-aryl[5H]pyrrolo[2,3-b]pyrazines

  摘要：

  We report a two step one-pot method for the synthesis of 2-bromo-6-aryl[5H]pyrrolo[2,3-b]pyrazines. The process makes use of a cleaner copper-free Sonogashira coupling and an improved base-mediated 5-exo-dig cyclisation to afford the products in good yields. This method expands the scope to structures that are poorly represented in the literature and incorporates a halide for further synthetic elaboration. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.02.005
• 作为产物：
  描述：

  苯乙炔 、 2-氨基-3,5-二溴吡嗪 在 bis-triphenylphosphine-palladium(II) chloride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以82%的产率得到5-bromo-3-(phenylethynyl)pyrazin-2-amine
  参考文献：
  名称：

  An efficient one-pot synthesis of 2-bromo-6-aryl[5H]pyrrolo[2,3-b]pyrazines

  摘要：

  We report a two step one-pot method for the synthesis of 2-bromo-6-aryl[5H]pyrrolo[2,3-b]pyrazines. The process makes use of a cleaner copper-free Sonogashira coupling and an improved base-mediated 5-exo-dig cyclisation to afford the products in good yields. This method expands the scope to structures that are poorly represented in the literature and incorporates a halide for further synthetic elaboration. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.02.005

文献信息

• COMPOUNDS USEFUL AS INHIBITORS OF ATR KINASE
  申请人：Charrier Jean-Damien

  公开号：US20120035408A1

  公开（公告）日：2012-02-09

  The present invention relates to pyrazine and pyridine compounds useful as inhibitors of ATR protein kinase. The invention also relates to pharmaceutically acceptable compositions comprising the compounds of this invention; methods of treating various diseases, disorders, and conditions using the compounds of this invention; processes for preparing the compounds of this invention; intermediates for the preparation of the compounds of this invention; and methods of using the compounds in in vitro applications, such as the study of kinases in biological and pathological phenomena; the study of intracellular signal transduction pathways mediated by such kinases; and the comparative evaluation of new kinase inhibitors. The compounds of this invention have formula V: wherein the variables are as defined herein.

  本发明涉及用作ATR蛋白激酶抑制剂的吡嗪和吡啶化合物。本发明还涉及包含该发明化合物的药学上可接受的组合物；使用该发明化合物治疗各种疾病、障碍和病症的方法；制备该发明化合物的过程；制备该发明化合物的中间体；以及在体外应用中使用该化合物的方法，例如研究生物和病理现象中的激酶、通过此类激酶介导的细胞内信号转导途径的研究以及新的激酶抑制剂的比较评估。本发明化合物的化学式为V，其中变量的定义如本文所述。
• Compounds useful as inhibitors of ATR kinase
  申请人：Charrier Jean-Damien

  公开号：US09062008B2

  公开（公告）日：2015-06-23

  The present invention relates to pyrazine and pyridine compounds useful as inhibitors of ATR protein kinase. The invention also relates to pharmaceutically acceptable compositions comprising the compounds of this invention; methods of treating various diseases, disorders, and conditions using the compounds of this invention; processes for preparing the compounds of this invention; intermediates for the preparation of the compounds of this invention; and methods of using the compounds in in vitro applications, such as the study of kinases in biological and pathological phenomena; the study of intracellular signal transduction pathways mediated by such kinases; and the comparative evaluation of new kinase inhibitors. The compounds of this invention have formula V: wherein the variables are as defined herein.

  本发明涉及用作ATR蛋白激酶抑制剂的吡嗪和吡啶化合物。本发明还涉及包含本发明化合物的药学上可接受的组合物；使用本发明化合物治疗各种疾病、疾病和病况的方法；制备本发明化合物的过程；制备本发明化合物的中间体；以及在体外应用中使用化合物的方法，如研究生物和病理现象中的激酶、介导这些激酶的细胞内信号转导途径的研究，以及新的激酶抑制剂的比较评估。本发明化合物具有公式V：其中变量如本文所定义。
• [EN] COMPOUNDS USEFUL AS INHIBITORS OF ATR KINASE<br/>[FR] COMPOSÉS UTILISABLES EN TANT QU'INHIBITEURS DE LA KINASE ATR
  申请人：VERTEX PHARMA

  公开号：WO2011143423A3

  公开（公告）日：2012-03-01
• US9062008B2
  申请人：——

  公开号：US9062008B2

  公开（公告）日：2015-06-23
• An efficient one-pot synthesis of 2-bromo-6-aryl[5H]pyrrolo[2,3-b]pyrazines
  作者：Iain Simpson、Steve A. St-Gallay、Stephen Stokes、David T.E. Whittaker、Rafal Wiewiora

  DOI：10.1016/j.tetlet.2015.02.005

  日期：2015.3

  We report a two step one-pot method for the synthesis of 2-bromo-6-aryl[5H]pyrrolo[2,3-b]pyrazines. The process makes use of a cleaner copper-free Sonogashira coupling and an improved base-mediated 5-exo-dig cyclisation to afford the products in good yields. This method expands the scope to structures that are poorly represented in the literature and incorporates a halide for further synthetic elaboration. (C) 2015 Elsevier Ltd. All rights reserved.