4-[3-Chloro-4-(1-methylimidazol-2-yl)sulfanylanilino]-7-fluoro-6-(2-thiomorpholin-4-ylethoxy)quinoline-3-carbonitrile | 1004994-58-4

• 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: 4-[3-Chloro-4-(1-methylimidazol-2-yl)sulfanylanilino]-7-fluoro-6-(2-thiomorpholin-4-ylethoxy)quinoline-3-carbonitrile
• CAS: 1004994-58-4
• 化学式: C₂₆H₂₄ClFN₆OS₂
• 分子量: 555.1
• InChiKey: RZPPFDDTLKTKHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  哌啶 、 4-[3-Chloro-4-(1-methylimidazol-2-yl)sulfanylanilino]-7-fluoro-6-(2-thiomorpholin-4-ylethoxy)quinoline-3-carbonitrile 在 N-甲基吡咯烷酮 、 sodium iodide 作用下， 以77%的产率得到4-[3-Chloro-4-(1-methylimidazol-2-yl)sulfanylanilino]-7-piperidin-1-yl-6-(2-thiomorpholin-4-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：

  硫代吗啉 、 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54%的产率得到4-[3-Chloro-4-(1-methylimidazol-2-yl)sulfanylanilino]-7-fluoro-6-(2-thiomorpholin-4-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

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.