3-{[3-[2-(3-chlorophenylamino)-pyrimidin-4-yl]-phenyl]-amino}-3-oxopropanoic acid methyl ester | 883199-29-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-{[3-[2-(3-chlorophenylamino)-pyrimidin-4-yl]-phenyl]-amino}-3-oxopropanoic acid methyl ester
• CAS: 883199-29-9
• 化学式: C₂₀H₁₇ClN₄O₃
• 分子量: 396.833
• InChiKey: XBISWWSXZWQEEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  93.21
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-{[3-[2-(3-chlorophenylamino)-pyrimidin-4-yl]-phenyl]-amino}-3-oxopropanoic acid methyl ester 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 5.25h， 以58%的产率得到3-{3-[2-(3-chlorophenylamino)-pyrimidin-4-yl]-phenylamino}-propanol
  参考文献：
  名称：

  Synthesis of analogs of the phenylamino-pyrimidine type protein kinase C inhibitor CGP 60474 utilizing a Negishi cross-coupling strategy

  摘要：

  Analogs of 3-{4-[2-(3-chlorophenylamino)-pyrimidin-4-yl]-pyridin-2-yl-amino}-propanol (CGP 60474) were synthesized as useful models for the evaluation of structure-activity relationships of phenylamino-pyrimidine-type protein kinase C inhibitors. The approach involved Pd-assisted cross-coupling as the key step. Negishi-type coupling was performed both with free amino functionalities and Boc-protected amines present and showed that the protection-cross-coupling-deprotection sequence leads to significantly higher yields. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.067
• 作为产物：
  描述：

  N-[3-(2-chloropyrimidin-4-yl)-phenyl]-carbamic acid 1,1-dimethylethyl ester 在 对甲苯磺酸 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 3-{[3-[2-(3-chlorophenylamino)-pyrimidin-4-yl]-phenyl]-amino}-3-oxopropanoic acid methyl ester
  参考文献：
  名称：

  Synthesis of analogs of the phenylamino-pyrimidine type protein kinase C inhibitor CGP 60474 utilizing a Negishi cross-coupling strategy

  摘要：

  Analogs of 3-{4-[2-(3-chlorophenylamino)-pyrimidin-4-yl]-pyridin-2-yl-amino}-propanol (CGP 60474) were synthesized as useful models for the evaluation of structure-activity relationships of phenylamino-pyrimidine-type protein kinase C inhibitors. The approach involved Pd-assisted cross-coupling as the key step. Negishi-type coupling was performed both with free amino functionalities and Boc-protected amines present and showed that the protection-cross-coupling-deprotection sequence leads to significantly higher yields. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.067