3-{[3-(2-chloropyrimidin-4-yl)-phenyl]-amino}-3-oxopropanoic acid methyl ester | 883199-28-8

• 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-chloropyrimidin-4-yl)-phenyl]-amino}-3-oxopropanoic acid methyl ester
• 英文别名: Methyl 3-[3-(2-chloropyrimidin-4-yl)anilino]-3-oxopropanoate；methyl 3-[3-(2-chloropyrimidin-4-yl)anilino]-3-oxopropanoate
• CAS: 883199-28-8
• 化学式: C₁₄H₁₂ClN₃O₃
• 分子量: 305.721
• InChiKey: ZRLUUCKWLSMRHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-{[3-(2-chloropyrimidin-4-yl)-phenyl]-amino}-3-oxopropanoic acid methyl ester 在 硼烷四氢呋喃络合物 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 9.25h， 生成 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 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 3-{[3-(2-chloropyrimidin-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

文献信息

• Synthesis of analogs of the phenylamino-pyrimidine type protein kinase C inhibitor CGP 60474 utilizing a Negishi cross-coupling strategy
  作者：Peter Stanetty、Jürgen Röhrling、Michael Schnürch、Marko D. Mihovilovic

  DOI：10.1016/j.tet.2005.11.067

  日期：2006.3

  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.