4-氯-7-(2-甲氧基乙氧基)-3-喹啉甲腈 | 622369-73-7

• 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
• 中文名称: 4-氯-7-(2-甲氧基乙氧基)-3-喹啉甲腈
• 英文名称: 4-chloro-7-(2-methoxyethoxy)-3-quinolinecarbonitrile
• 英文别名: 4-chloro-7-(2-methoxyethoxy)quinoline-3-carbonitrile
• CAS: 622369-73-7
• 化学式: C₁₃H₁₁ClN₂O₂
• 分子量: 262.696
• InChiKey: NKNHPOUWDIAROH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-氯-7-(2-甲氧基乙氧基)-3-喹啉甲腈 、 2,4-二氯苯胺 在 吡啶盐酸盐 作用下， 以 乙二醇乙醚 为溶剂， 反应 0.5h， 生成 4-[(2,4-Dichlorophenyl)amino]-7-(2-methoxyethoxy)quinoline-3-carbonitrile
  参考文献：
  名称：

  Process for the preparation of 7-substituted-3 quinolinecarbonitriles

  摘要：

  提供了一种制备7-取代-3-喹啉羰基腈和中间体的方法，该中间体在制备7-取代-3-喹啉羰基腈和药用可接受盐的过程中有用。将7-氟-4-氧代-1,4-二氢-3-喹啉羰基腈转化为7-取代-3-喹啉羰基腈，经过三个步骤，这些化合物抑制某些蛋白激酶的作用，并在癌症治疗中有用。

  公开号：

  US20030212276A1
• 作为产物：
  描述：

  7-(2-methoxyethoxy)-4-oxo-1,4-dihydro-3-quinolinecarbonitrile 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 反应 1.0h， 以87%的产率得到4-氯-7-(2-甲氧基乙氧基)-3-喹啉甲腈
  参考文献：
  名称：

  Facile preparation of new 4-phenylamino-3-quinolinecarbonitrile Src kinase inhibitors via 7-fluoro intermediates: Identification of potent 7-amino analogs

  摘要：

  A more efficient preparation of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-7-fluoro-6-methoxy-3-quinolinecarbonitrile (2), the penultimate intermediate in the synthesis of bosutinib (1a), was developed. New 7-alkoxy-4-phenylamino-3-quinolinecarbonitrile Src inhibitors were prepared from 5 and 9, the 6-ethoxy and 6-hydrogen analogs of 2. In addition, the fluoro group of 2 was readily displaced by primary and secondary amines to give 7-amino analogs. Two of these 7-amino analogs, 15 and 18, were potent Src inhibitors with in vivo activity. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.09.028

文献信息

• Process for the preparation of 7-substituted-3 quinolinecarbonitriles
  申请人：Wyeth Holdings Corporation

  公开号：US20030212276A1

  公开（公告）日：2003-11-13

  There is provided a process for the preparation of 7-substituted-3-quinolinecarbonitriles and intermediates useful in a process to prepare 7-substituted-3-quinolinecarbonitriles and pharmaceutically acceptable salts is described. Where 7-fluoro-4-oxo-1,4-dihydro-3-quinolinecarbonitrile is converted in three steps to 7-substituted-3-quinolinecarbonitriles which inhibit the action of certain protein kinases and are useful in the treatment of cancer.

  提供了一种制备7-取代-3-喹啉羰基腈和中间体的方法，该中间体在制备7-取代-3-喹啉羰基腈和药用可接受盐的过程中有用。将7-氟-4-氧代-1,4-二氢-3-喹啉羰基腈转化为7-取代-3-喹啉羰基腈，经过三个步骤，这些化合物抑制某些蛋白激酶的作用，并在癌症治疗中有用。
• [EN] PROCESS FOR THE PREPARATION OF 7-SUBSTITUTED-3-QUINOLINE AND 3-QUINOL-4-ONE CARBONITRILES<br/>[FR] PREPARATION DE 3-QUINOLINE ET DE 3-QUINOL- 4-ONE CARBONITRILES SUBSTITUES EN POSITION 7
  申请人：WYETH CORP

  公开号：WO2003093241A1

  公开（公告）日：2003-11-13

  There is provided a process for the preparation of 7-substituted-3-quinolinecarbonitriles and intermediates useful in a process to prepare 7-substituted-3-quinolinecarbonitriles and pharmaceutically acceptable salts is described. Where 7-fluoro-4-oxo-1,4-dihydro-3-quinolinecarbonitrile is converted in three steps to 7-substituted-3-quinolinecarbonitriles which inhibit the action of certain protein kinases and are useful in the treatment of cancer.

  提供了一种制备7-取代-3-喹啉羰基腈及其中间体的方法，该中间体可用于制备7-取代-3-喹啉羰基腈及其药用可接受盐的方法。其中，7-氟-4-氧代-1,4-二氢-3-喹啉羰基腈经过三步转化成为抑制某些蛋白激酶作用且用于治疗癌症的7-取代-3-喹啉羰基腈。
• PROCESS FOR THE PREPARATION OF 7-SUBSTITUTED-3-QUINOLINE AND 3-QUINOL-4-ONE CARBONITRILES
  申请人：Wyeth Holdings Corporation

  公开号：EP1499594A1

  公开（公告）日：2005-01-26
• US6780996B2
  申请人：——

  公开号：US6780996B2

  公开（公告）日：2004-08-24
• Facile preparation of new 4-phenylamino-3-quinolinecarbonitrile Src kinase inhibitors via 7-fluoro intermediates: Identification of potent 7-amino analogs
  作者：Diane H. Boschelli、Biqi Wu、Fei Ye、Haris Durutlic、Jennifer M. Golas、Judy Lucas、Frank Boschelli

  DOI：10.1016/j.bmc.2007.09.028

  日期：2008.1

  A more efficient preparation of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-7-fluoro-6-methoxy-3-quinolinecarbonitrile (2), the penultimate intermediate in the synthesis of bosutinib (1a), was developed. New 7-alkoxy-4-phenylamino-3-quinolinecarbonitrile Src inhibitors were prepared from 5 and 9, the 6-ethoxy and 6-hydrogen analogs of 2. In addition, the fluoro group of 2 was readily displaced by primary and secondary amines to give 7-amino analogs. Two of these 7-amino analogs, 15 and 18, were potent Src inhibitors with in vivo activity. (c) 2007 Elsevier Ltd. All rights reserved.