6-(2-Chloroethoxy)-4-[3-chloro-4-(1-methylimidazol-2-yl)sulfanylanilino]-7-fluoroquinoline-3-carbonitrile | 1004994-49-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-(2-Chloroethoxy)-4-[3-chloro-4-(1-methylimidazol-2-yl)sulfanylanilino]-7-fluoroquinoline-3-carbonitrile
• 英文别名: 6-(2-chloroethoxy)-4-[3-chloro-4-(1-methylimidazol-2-yl)sulfanylanilino]-7-fluoroquinoline-3-carbonitrile
• CAS: 1004994-49-3
• 化学式: C₂₂H₁₆Cl₂FN₅OS
• 分子量: 488.372
• InChiKey: DGFNDGKPAITDJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  四氢吡咯 、 6-(2-Chloroethoxy)-4-[3-chloro-4-(1-methylimidazol-2-yl)sulfanylanilino]-7-fluoroquinoline-3-carbonitrile 在 N-甲基吡咯烷酮 、 sodium iodide 作用下， 以40%的产率得到4-[3-Chloro-4-(1-methylimidazol-2-yl)sulfanylanilino]-7-pyrrolidin-1-yl-6-(2-pyrrolidin-1-ylethoxy)quinoline-3-carbonitrile
  参考文献：
  名称：

  Observation of differential reactivity of cyclic amines in SN2 and SNAr displacement reactions in the course of synthesizing C-6, C-7 substituted quinolinecarbonitrile MEK1 kinase inhibitors

  摘要：

  We have previously reported on a series of 4-anilino-6,7-dialkoxy-3-quinolinecarbonitriles as potent inhibitors of MEK1 kinase. Herein, we describe our synthetic efforts toward a series of 4-anilino-6-allcoxy-7-amino-3-quinolinecarbonitriles. In the course of this work, we were able to rapidly construct a library of 4-anilino-6-alkoxy-7-amino-3-quinolinecarbonitriles by simultaneous or sequential S(N)2 (displacement) reactions on the C-6 chloroalkoxy moiety and SNAr (addition/elimination) reactions at C-7 with nucleophilic amines. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.10.151
• 作为产物：
  描述：

  、 2-氯乙基对甲苯磺酸酯 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 6-(2-Chloroethoxy)-4-[3-chloro-4-(1-methylimidazol-2-yl)sulfanylanilino]-7-fluoroquinoline-3-carbonitrile
  参考文献：
  名称：

  Observation of differential reactivity of cyclic amines in SN2 and SNAr displacement reactions in the course of synthesizing C-6, C-7 substituted quinolinecarbonitrile MEK1 kinase inhibitors

  摘要：

  We have previously reported on a series of 4-anilino-6,7-dialkoxy-3-quinolinecarbonitriles as potent inhibitors of MEK1 kinase. Herein, we describe our synthetic efforts toward a series of 4-anilino-6-allcoxy-7-amino-3-quinolinecarbonitriles. In the course of this work, we were able to rapidly construct a library of 4-anilino-6-alkoxy-7-amino-3-quinolinecarbonitriles by simultaneous or sequential S(N)2 (displacement) reactions on the C-6 chloroalkoxy moiety and SNAr (addition/elimination) reactions at C-7 with nucleophilic amines. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.10.151

文献信息

• Observation of differential reactivity of cyclic amines in SN2 and SNAr displacement reactions in the course of synthesizing C-6, C-7 substituted quinolinecarbonitrile MEK1 kinase inhibitors
  作者：Darrin W. Hopper、Minu Dutia、Dan M. Berger、Dennis W. Powell

  DOI：10.1016/j.tetlet.2007.10.151

  日期：2008.1

  We have previously reported on a series of 4-anilino-6,7-dialkoxy-3-quinolinecarbonitriles as potent inhibitors of MEK1 kinase. Herein, we describe our synthetic efforts toward a series of 4-anilino-6-allcoxy-7-amino-3-quinolinecarbonitriles. In the course of this work, we were able to rapidly construct a library of 4-anilino-6-alkoxy-7-amino-3-quinolinecarbonitriles by simultaneous or sequential S(N)2 (displacement) reactions on the C-6 chloroalkoxy moiety and SNAr (addition/elimination) reactions at C-7 with nucleophilic amines. (c) 2007 Elsevier Ltd. All rights reserved.