3-(2-amino-4-(3-chloropropoxy)-5-methoxyphenyl)-3-oxopropanenitrile | 1637593-19-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2-amino-4-(3-chloropropoxy)-5-methoxyphenyl)-3-oxopropanenitrile
• 英文别名: 3-[2-Amino-4-(3-chloropropoxy)-5-methoxyphenyl]-3-oxopropanenitrile；3-[2-amino-4-(3-chloropropoxy)-5-methoxyphenyl]-3-oxopropanenitrile
• CAS: 1637593-19-1
• 化学式: C₁₃H₁₅ClN₂O₃
• 分子量: 282.727
• InChiKey: KZQWYCINIHIXFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(2-amino-4-(3-chloropropoxy)-5-methoxyphenyl)-3-oxopropanenitrile 在 三氯氧磷 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 为溶剂， 反应 4.0h， 生成 4-氯-7-(3-氯丙氧基)-3-氰基-6-甲氧基喹啉
  参考文献：
  名称：

  New Synthetic Process for Bosutinib

  摘要：

  A new and improved synthetic route to bosutinib is described on a hectogram scale. The key step is the intramolecular cyclization of a 3-(2-aminophenyl)-3-oxopropanenitrile with N,N-dimethylformamide dimethyl acetal to form the 3-cyano-4-hydroxyquinoline ring of 7-(3-chloropropoxy)-6-methoxy-4-oxo-1,4-dihydroquinoline-3-carbonitrile. A practical synthetic method to 2,4-dichloro-5-methoxyaniline is also established. Bosutinib is obtained in 18.0% yield over nine steps from acetovanillone with 98.9% purity (HPLC).

  DOI：

  10.1055/s-0035-1560471
• 作为产物：
  描述：

  1-(4-(3-chloropropoxy)-5-methoxy-2-nitrophenyl)ethanone 在 氢气 、 溴 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 13.0h， 生成 3-(2-amino-4-(3-chloropropoxy)-5-methoxyphenyl)-3-oxopropanenitrile
  参考文献：
  名称：

  New Synthetic Process for Bosutinib

  摘要：

  A new and improved synthetic route to bosutinib is described on a hectogram scale. The key step is the intramolecular cyclization of a 3-(2-aminophenyl)-3-oxopropanenitrile with N,N-dimethylformamide dimethyl acetal to form the 3-cyano-4-hydroxyquinoline ring of 7-(3-chloropropoxy)-6-methoxy-4-oxo-1,4-dihydroquinoline-3-carbonitrile. A practical synthetic method to 2,4-dichloro-5-methoxyaniline is also established. Bosutinib is obtained in 18.0% yield over nine steps from acetovanillone with 98.9% purity (HPLC).

  DOI：

  10.1055/s-0035-1560471

文献信息

• A New and Practical Synthesis of 7-(3-Chloropropoxy)-6-methoxy-4-oxo-1,4-dihydroquinoline-3-carbonitrile
  作者：Han Wang、Yongjun Mao、Jianfeng Qin、Haijun He、Gang Liu、Bingyi Gao

  DOI：10.3987/com-14-13023

  日期：——
• New Synthetic Process for Bosutinib
  作者：Yongjun Mao、Chunping Zhu、Ziyang Kong、Jiao Wang、Guoqing Zhu、Xinfeng Ren

  DOI：10.1055/s-0035-1560471

  日期：——

  A new and improved synthetic route to bosutinib is described on a hectogram scale. The key step is the intramolecular cyclization of a 3-(2-aminophenyl)-3-oxopropanenitrile with N,N-dimethylformamide dimethyl acetal to form the 3-cyano-4-hydroxyquinoline ring of 7-(3-chloropropoxy)-6-methoxy-4-oxo-1,4-dihydroquinoline-3-carbonitrile. A practical synthetic method to 2,4-dichloro-5-methoxyaniline is also established. Bosutinib is obtained in 18.0% yield over nine steps from acetovanillone with 98.9% purity (HPLC).