6-methyl-N1-(pyrimidin-2-yl)benzene-1,3-diamine | 734533-16-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-methyl-N1-(pyrimidin-2-yl)benzene-1,3-diamine
• 英文别名: 4-methyl-3-N-pyrimidin-2-ylbenzene-1,3-diamine
• CAS: 734533-16-5
• 化学式: C₁₁H₁₂N₄
• 分子量: 200.243
• InChiKey: ZTCBNVURBQXILL-UHFFFAOYSA-N

物化性质

• 沸点：
  403.6±55.0 °C(Predicted)
• 密度：
  1.247±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  63.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苯甲酸甲酯 、 6-methyl-N1-(pyrimidin-2-yl)benzene-1,3-diamine 在 二(三甲基铝)-1,4-二氮杂二环[2.2.2]辛烷加合物 作用下， 以 四氢呋喃 为溶剂， 反应 0.13h， 以97%的产率得到N-(4-methyl-3-(pyrimidin-2-ylamino)phenyl)benzamide
  参考文献：
  名称：

  Investigating Scale-Up and Further Applications of DABAL-Me₃ Promoted Amide Synthesis

  摘要：

  Methods for the batch scale up of DABAL-Me-3 promoted direct ester to amide synthesis have been demonstrated at 10-100 g scales using a tert-amide model compound. Procedures for 20 g scale couplings in standard laboratory glassware and up to 0.1 kg in industry-standard jacketed glass reactors in near quantitative yields are given. A derivative of the anticancer agent Imatinib (Gleevec) has been synthesized on a 26 g scale (98% yield, >98% purity) establishing DABAL-Me-3 as a potential alternative for the synthesis of amides in API scale preparations. Continuous flow methodology provides a method for larger scales (productivities of >50 g h(-1)). In addition, nitriles were coupled to primary amines and hydrazines with DABAL-Me-3, resulting in the clean formation of free amidines (16 examples) and amidrazones.

  DOI：

  10.1021/acs.oprd.5b00101

文献信息

• Enzyme modulators and treatments
  申请人：Flynn L. Daniel

  公开号：US20070078121A1

  公开（公告）日：2007-04-05

  Novel compounds and methods of using those compounds for the treatment of inflammatory conditions, immunological disorders, hyperproliferative diseases, cancer, and diseases characterized by hyper-vascularization are provided. In a preferred embodiment, modulation of the activation state of kinases, including p38 kinase protein, abl kinase protein, bcr-abl kinase protein, braf kinase protein, VEGFR kinase protein, or PDGFR kinase protein, comprises the step of contacting said kinase protein with the novel compounds.

  提供了新型化合物及其使用方法，用于治疗炎症性疾病、免疫性疾病、过度增生性疾病、癌症以及以高血管化为特征的疾病。在一种优选实施方式中，调节激酶的激活状态，包括p38激酶蛋白、abl激酶蛋白、bcr-abl激酶蛋白、braf激酶蛋白、VEGFR激酶蛋白或PDGFR激酶蛋白，包括将该激酶蛋白与新型化合物接触的步骤。
• ENZYME MODULATORS AND TREATMENTS
  申请人：Flynn L. Daniel

  公开号：US20080113967A1

  公开（公告）日：2008-05-15

  Novel compounds and methods of using those compounds for the treatment of inflammatory conditions, hyperproliferative diseases, cancer, and diseases characterized by hyper-vascularization are provided. In a preferred embodiment, modulation of the activation state of p38 kinase protein, abl kinase protein, ber-abl kinase protein, braf kinase protein, VEGFR kinase protein, or PDGFR kinase protein comprises the step of contacting said kinase protein with the novel compounds.

  本发明提供了新的化合物及其使用方法，用于治疗炎症状况、过度增殖性疾病、癌症和以高血管化为特征的疾病。在优选实施例中，调节p38激酶蛋白、abl激酶蛋白、ber-abl激酶蛋白、braf激酶蛋白、VEGFR激酶蛋白或PDGFR激酶蛋白的激活状态，包括将该激酶蛋白与新的化合物接触的步骤。
• US7279576B2
  申请人：——

  公开号：US7279576B2

  公开（公告）日：2007-10-09
• US8163756B2
  申请人：——

  公开号：US8163756B2

  公开（公告）日：2012-04-24
• Investigating Scale-Up and Further Applications of DABAL-Me₃ Promoted Amide Synthesis
  作者：Darren S. Lee、Zacharias Amara、Martyn Poliakoff、Thomas Harman、Gary Reid、Barrie Rhodes、Steve Brough、Thomas McInally、Simon Woodward

  DOI：10.1021/acs.oprd.5b00101

  日期：2015.7.17

  Methods for the batch scale up of DABAL-Me-3 promoted direct ester to amide synthesis have been demonstrated at 10-100 g scales using a tert-amide model compound. Procedures for 20 g scale couplings in standard laboratory glassware and up to 0.1 kg in industry-standard jacketed glass reactors in near quantitative yields are given. A derivative of the anticancer agent Imatinib (Gleevec) has been synthesized on a 26 g scale (98% yield, >98% purity) establishing DABAL-Me-3 as a potential alternative for the synthesis of amides in API scale preparations. Continuous flow methodology provides a method for larger scales (productivities of >50 g h(-1)). In addition, nitriles were coupled to primary amines and hydrazines with DABAL-Me-3, resulting in the clean formation of free amidines (16 examples) and amidrazones.