N-(2-bromoacetyl)cyclopropanecarboxamide | 1175127-58-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2-bromoacetyl)cyclopropanecarboxamide
• CAS: 1175127-58-8
• 化学式: C₆H₈BrNO₂
• 分子量: 206.039
• InChiKey: OHBVANZDLRWERZ-UHFFFAOYSA-N

物化性质

• 沸点：
  311.6±21.0 °C(Predicted)
• 密度：
  1.715±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-bromoacetyl)cyclopropanecarboxamide 在 potassium phosphate 、 caesium carbonate 作用下， 以 N,N-二甲基乙酰胺 、 二甲基亚砜 为溶剂， 反应 10.0h， 生成 N-(5-{[2-(cyclopropanecarboxamido)imidazo[1,2-b]pyridazin-6-yl]oxy}-2-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide
  参考文献：
  名称：

  Convergent and streamlined synthesis of 6-etherified imidazo[1,2-b]pyridazine-2-amine derivatives possessing VEGFR-2 kinase inhibitory activity

  摘要：

  A convergent and streamlined synthesis of selective vascular endothelial growth factor receptor (VEGFR) 2 kinase inhibitors has been achieved using a synthetic strategy based on an SNAr reaction of 6-chloroimidazo[1,2-b]pyridazine with phenols in the final step. For the synthesis of 6-chloroimidazo[1,2-b]pyridazine, a one-pot reaction using 3-amino-6-chloropyridazine, cyclopropanecarboxamide, and bromoacetyl bromide was developed. The phenols were easily prepared by chemoselective acylation of 3-aminophenols with pyrazole carboxylic acids, and an efficient and high-yielding synthesis of N-ethylpyrazole was also developed. The SNAr reaction of 6-chloroimidazo[1,2-b]pyridazine with phenols in DMSO in the presence of cesium carbonate successfully proceeded at 100-110 degrees C to give the target products in good yields. This new chromatography-free process will be not only useful for the further bulk supply of these compounds but also applicable to the synthesis of other compounds containing the 6-etherified imidazo[1,2-b]pyridazin-2-amine core. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.087
• 作为产物：
  描述：

  环丙酰胺 、 溴乙酰溴 在 乙酸乙酯 、 碳酸氢钠 、 水 、 Brine 、 Sodium sulfate-III 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以to get N-(2-bromoacetyl)cyclopropanecarboxamide (138 g, 670 mmol, 97% yield) as an off white solid的产率得到N-(2-bromoacetyl)cyclopropanecarboxamide
  参考文献：
  名称：

  COMBINATION OF A cMET INHIBITOR AND AN ANTIBODY TO HGF AND/OR cMET

  摘要：

  治疗疾病状态的方法，其中HGF/cMET具有对疾病状态的病理学和/或症状学有贡献的活性，以及用于实践这些方法的工具包和制品。

  公开号：

  US20130315895A1

文献信息

• [EN] HETEROARYLAMIDE INHIBITORS OF TBK1<br/>[FR] INHIBITEURS HÉTÉROARYLAMIDE DE TBK1
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2015134171A1

  公开（公告）日：2015-09-11

  The present invention provides compounds of formula 1: which are useful as inhibitors of TBK-1, pharmaceutical compositions thereof, methods for treatment of conditions associated with TBK1, processes for making the compounds and intermediates thereof.

  本发明提供了化合物的公式1：这些化合物可用作TBK-1的抑制剂，以及与之相关的药物组合物、治疗与TBK1相关疾病的方法、制备这些化合物及其中间体的工艺。
• [EN] cMET INHIBITORS<br/>[FR] INHIBITEURS DE CMET
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2010019899A1

  公开（公告）日：2010-02-18

  Compounds of the following formula are provided for use with cMET: wherein the variables are as defined herein. Also provided are pharmaceutical compositions, kits and articles of manufacture comprising such compounds; methods and intermediates useful for making the compounds; and methods of using said compounds.

  提供以下公式的化合物供与cMET一起使用：其中变量如本文所定义。还提供包含这些化合物的药物组合物、试剂盒和制造物品；用于制备这些化合物的有用中间体和方法；以及使用这些化合物的方法。
• cMET INHIBITORS
  申请人：Bressi Jerome C.

  公开号：US20100063054A1

  公开（公告）日：2010-03-11

  Compounds of the following formula are provided for use with cMET: wherein the variables are as defined herein. Also provided are pharmaceutical compositions, kits and articles of manufacture comprising such compounds; methods and intermediates useful for making the compounds; and methods of using said compounds.

  提供以下公式化合物用于cMET的使用：其中变量如此处所定义。还提供了包含这些化合物的制药组合物、工具箱和制造物品，以及用于制造这些化合物的有用中间体和方法，以及使用这些化合物的方法。
• cMET inhibitors
  申请人：Takeda Pharmaceutical Company Limited

  公开号：US08178534B2

  公开（公告）日：2012-05-15

  Compounds of the following formula are provided for use with cMET: wherein the variables are as defined herein. Also provided are pharmaceutical compositions, kits and articles of manufacture comprising such compounds; methods and intermediates useful for making the compounds; and methods of using the compounds.

  提供以下公式的化合物供cMET使用：其中变量的定义如本文所述。还提供了包含这些化合物的制药组合物、工具包和制造物品；用于制备这些化合物的方法和中间体；以及使用这些化合物的方法。
• HETEROARYLAMIDE INHIBITORS OF TBK1
  申请人：KWOK Lily

  公开号：US20170015669A1

  公开（公告）日：2017-01-19

  The present invention provides compounds of formula 1: which are useful as inhibitors of TBK-1, pharmaceutical compositions thereof, methods for treatment of conditions associated with TBK1, processes for making the compounds and intermediates thereof.