2-methyl-4-N-phenylaminoquinazoline | 57942-18-4

• 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: 2-methyl-4-N-phenylaminoquinazoline
• 英文别名: 2-methyl-N-phenylquinazolin-4-amine；2-methyl-4-anilinoquinazoline；(2-methyl-quinazolin-4-yl)-phenyl-amine；4-Anilino-2-methylchinazolin
• CAS: 57942-18-4
• 化学式: C₁₅H₁₃N₃
• 分子量: 235.288
• InChiKey: RCWRELVGMCLUAW-UHFFFAOYSA-N

物化性质

• 熔点：
  175-178 °C
• 沸点：
  328.8±24.0 °C(Predicted)
• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-甲基-4(3H)-喹唑酮 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 1.0h， 生成 2-methyl-4-N-phenylaminoquinazoline
  参考文献：
  名称：

  Synthesis of Substituted Quinazolines: Application to the Synthesis of Verubulin

  摘要：

  Through newly adapted methodology, 2-methyl-3H-quinazolin-4-one was activated using a number of methods followed by displacement to afford 4-aminoquinazolines. The most useful of these processes utilize the p-toluenesulfonate ester or I-2/PPh3 activation. Using this methodology, the anticancer vascular targeting clinical candidate verubulin (1) was synthesized in a highly efficient manner.

  DOI：

  10.1080/00397911.2010.529730

文献信息

• 8-[3-amino-piperidin-1-yl]-xanthines, their preparation and their use as pharmaceutical compositions
  申请人：Himmelsbach Frank

  公开号：US20050234108A1

  公开（公告）日：2005-10-20

  The present invention relates to substituted xanthines of general formula wherein R is defined as in claim 1 , the tautomers, the stereoisomers, the mixtures thereof and the salts thereof, which have valuable pharmacological properties, particularly an inhibiting effect on the activity of the enzyme dipeptidylpeptidase-IV (DPP-IV).

  本发明涉及通式所示的取代黄嘌呤，其中R如权利要求书中所定义，其互变体、立体异构体、其混合物和盐具有有价值的药理特性，特别是对酶二肽基肽酶-IV（DPP-IV）活性的抑制作用。
• Syntheses of Some 4-Anilinoquinazoline Derivatives
  作者：Roberto Rittner、Silvana A. Rocco、José Eduardo Barbarini

  DOI：10.1055/s-2004-815949

  日期：——

  Some 4-N-(3'- or 4'-substituted-phenyl)amino-6,7-dimethoxyquinazolines and the corresponding unsubstituted compounds were synthesized from 2-amino-4,5-dimethoxybenzoic acid and the appropriate substituted anilines. Other related quinazolines or their synthetic intermediates were also obtained. A large number of the described quinazolines are new compounds, while the remaining were prepared by a more

  一些4-N-(3'-或4'-取代-苯基)氨基-6,7-二甲氧基喹唑啉和相应的未取代化合物由2-氨基-4,5-二甲氧基苯甲酸和适当的取代苯胺合成。还获得了其他相关的喹唑啉或其合成中间体。大量描述的喹唑啉是新化合物，而其余的则通过更有效的方法制备。合成这些化合物的主要目标是 4-苯胺基喹唑啉药效团是一个重要的单元，它存在于几种蛋白激酶的 ATP 竞争性抑制剂中。
• 8-[3-AMINO-PIPERIDIN-1-YL]-XANTHINES, THEIR PREPARATION AND THEIR USE AS PHARMACEUTICAL COMPOSITIONS
  申请人：HIMMELSBACH Frank

  公开号：US20090137801A1

  公开（公告）日：2009-05-28

  Disclosed are substituted xanthines of the formula wherein R is defined as in claim 1 , the tautomers, the stereoisomers, the mixtures thereof and the salts thereof, which have valuable pharmacological properties, particularly an inhibiting effect on the activity of the enzyme dipeptidylpeptidase-IV (DPP-IV).

  本发明涉及一种公式如下的取代黄嘌呤：其中R如权利要求1所定义，其互变异构体、立体异构体、混合物及其盐，具有有价值的药理学特性，特别是对酶二肽基肽酶-IV（DPP-IV）的抑制作用。
• Polyphosphoric Acid Esters Promoted Synthesis of Quinazolin-4(3<i>H</i>)-imines from 2-Aminobenzonitrile
  作者：Natalia B. Kilimciler、Nicolás M. Palavecino、Nadia Gruber、Daniel R. Vega、Liliana R. Orelli、Jimena E. Díaz

  DOI：10.1021/acs.joc.2c02558

  日期：——

  A novel method for the synthesis of quinazolin-4(3H)-imines (QIs) by trimethylsilyl polyphosphate (PPSE) promoted reaction of 2-aminobenzonitrile with secondary amides is reported. The reaction is general and allows for the synthesis of N3-aryl and N3-alkyl QIs with variable 2-substituents affording high yields. The procedure was extended to derivatives bearing additional functional groups. The method

  报道了一种通过三甲基硅烷基聚磷酸酯 （PPSE） 促进 2-氨基苯腈与仲酰胺反应合成喹唑啉-4（3H）-亚胺 （QI） 的新方法。该反应是一般反应，允许合成 N3-芳基和 N3-烷基 QI，具有可变的 2-取代基，产量高。该程序扩展到带有额外官能团的衍生物。该方法操作简单，涉及容易获得的起始材料和温和的脱水剂，具有广泛的官能团耐受性。该反应程序被证明适用于放大。根据文献数据和实验观察，提出了一种通过中间腈离子的可能反应路径。
• A new DMAP-catalyzed and microwave-assisted approach for introducing heteroarylamino substituents at position-4 of the quinazoline ring
  作者：Armand Gellis、Charline Kieffer、Nicolas Primas、Gilles Lanzada、Michel Giorgi、Pierre Verhaeghe、Patrice Vanelle

  DOI：10.1016/j.tet.2014.09.024

  日期：2014.11

  We report herein a new methodology for synthesizing quinazoline derivatives bearing a heteroarylamino moiety at position-4 of the quinazoline ring. As an alternative to the Buchwald-Hartwig cross-coupling reaction, which appears, until now, as the only efficient way to react 4-chloroquinazolines with numerous amino nitrogen-containing heterocycles displaying poor nucleophilicity, we developed a DMAP-catalyzed reaction involving microwave irradiation. Optimization of the reaction conditions led to the use of 30 mol % of DMAP in toluene, using a monomode microwave reactor and sealed vials. Moreover, the SNAr reaction intermediate salt was isolated and fully characterized. Finally, the procedure was extended to two different 2-substituted-quinazoline series and also to various anilines, demonstrating that this approach was a general efficient way to access to such 4-substituted quinazoline scaffolds of high pharmaceutical interest. (C) 2014 Elsevier Ltd. All rights reserved.