7-(benzyloxy)-4-[(5-chloro-1,3-benzodioxol-4-yl)amino]-quinazolin-5-ol | 1241906-31-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 7-(benzyloxy)-4-[(5-chloro-1,3-benzodioxol-4-yl)amino]-quinazolin-5-ol
• CAS: 1241906-31-9
• 化学式: C₂₂H₁₆ClN₃O₄
• 分子量: 421.84
• InChiKey: IMWONWXDCXGPJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.04
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  85.73
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  7-(benzyloxy)-4-[(5-chloro-1,3-benzodioxol-4-yl)amino]-quinazolin-5-ol 在 偶氮二甲酸二叔丁酯 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 12.12h， 生成 4-chloro-3-((7-(2-(4-methylpiperazin-1-yl)ethoxy)-5-((tetrahydro-2H-pyran-4-yl)oxy)quinazolin-4-yl)amino)benzene-1,2-diol
  参考文献：
  名称：

  Process Research and Development for the Kilogram Manufacture of the SRC Kinase Inhibitor AZD0530

  摘要：

  Process research and development of a synthetic route towards a novel SRC kinase inhibitor is described. The Medicinal Chemistry route was very long and suffered from extensive use of chlorinated solvents and chromatography. A number of steps in the Medicinal Chemistry route were also unattractive for large-scale use for a variety of reasons. The route was modified to produce a shorter synthetic scheme that started from more readily available materials. By using the modified route, the title compound was manufactured on kilogram scale without recourse to chromatography and in significantly fewer steps. The scaled synthesis required two Mitsunobu couplings, which were developed and scaled successfully. An interesting hydrazine impurity was identified in the second Mitsunobu coupling; a mechanism for its formation is proposed, and a method for its control is described. The formation and control of some other interesting impurities are also described.

  DOI：

  10.1021/op100161y
• 作为产物：
  描述：

  以91.1的产率得到7-(benzyloxy)-4-[(5-chloro-1,3-benzodioxol-4-yl)amino]-quinazolin-5-ol
  参考文献：
  名称：

  Org. Process. Res. Dev. 2010, 14, 1078-1087

  摘要：

  DOI：