4-Amino-3-cyanoquinolin | 36626-03-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-Amino-3-cyanoquinolin
• 英文别名: 4-amino-quinoline-3-carbonitrile；4-Aminoquinoline-3-carbonitrile
• CAS: 36626-03-6
• 化学式: C₁₀H₇N₃
• mdl: MFCD11868746
• 分子量: 169.186
• InChiKey: VBMNWPOIPHHUSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Amino-3-cyanoquinolin 、 sodium hydroxide 以72%的产率得到
  参考文献：
  名称：

  SCHAEFER H.; GEWALD K., MONATSH. CHEM., 1978, 109, NO 3, 527-535

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(2,2-dicyanovinyl)-aniline 在 三氯化铝 作用下， 反应 1.0h， 以96%的产率得到4-Amino-3-cyanoquinolin
  参考文献：
  名称：

  具有正性肌力活性的化合物，III1)：作为潜在正性肌力药物的 4-氨基喹啉衍生物的合成

  摘要：

  苯胺基丙烯酸衍生物 2-4 是关键中间体，从中可以合成 1-烷基取代的 4-氨基喹啉 10-15 和 4-烷基氨基喹啉衍生物 16-23，并检查对来自几内亚的离体左心房和乳头肌的正性肌力活性猪。构效关系表明效果取决于目标化合物的烷基侧链。

  DOI：

  10.1002/ardp.19903230911

文献信息

• Methods of synthesizing substituted 3-cyanoquinolines and intermediates thereof
  申请人：Chew Warren

  公开号：US20060270668A1

  公开（公告）日：2006-11-30

  The invention is directed to methods of making substituted 3-cyanoquinolines, including compounds according to the following formula: The methods are amenable to large scale manufacture, avoid the use of chromatographic separations, and provide stable, high purity product more efficiently than in the prior art.

  本发明涉及制备取代的3-氰基喹啉的方法，包括根据以下公式所示的化合物：这些方法适用于大规模生产，避免了色谱分离的使用，并且比现有技术更有效地提供了稳定、高纯度的产品。
• Process for preparation of 4-amino-3-quinolinecarbonitriles
  申请人：Sutherland Wiggins Karen

  公开号：US20050043537A1

  公开（公告）日：2005-02-24

  This invention discloses a process for the preparation of a 4-amino-3-quinolinecarbonitrile comprising combining an amine compound with a cyanoacetic acid and an acid catalyst to yield a cyanoacetamide; condensing the cyanoacetamide with an optionally up to tetra-substituted aniline in an alcoholic solvent and a trialkylorthoformate to yield a 3-amino-2-cyanoacrylamide; combining the 3-amino-2-cyanoacrylamide with phosphorus oxychloride in acetonitrile, butyronitrile, toluene or xylene, optionally in the presence of a catalyst to yield a 4-amino-3-quinolinecarbonitrile and also discloses a process for the preparation of a 7-amino-thieno[3,2-b]pyridine-6-carbonitrile comprising combining a disubstituted 3-amino thiophene with a cyanoacetamide and trialkylorthoformate in an alcoholic solvent to obtain a 3-amino-2-cyanoacrylamide; and combining the 3-amino-2-cyanoacrylamide with phosphorus oxychloride and acetonitrile, butyronitrile, toluene or xylene, optionally in the presence of a catalyst to yield a 7-amino-thieno[3,2-b]pyridine-6-carbonitrile and also discloses a process for the preparation of a 4-amino-3-quinolinecarbonitrile by combining an amine compound with a cyanoacetic acid and a peptide coupling reagent to obtain a suspension; filtering the suspension to yield a cyanoacetamide; condensing the cyanoacetamide with an optionally up to tetra-substituted aniline, an alcoholic solvent, and triethylorthoformate to yield a 3-amino-2-cyanoacrylamide; and combining the 3-amino-2-cyanoacrylamide with phosphorus oxychloride to yield a 4-amino-3-quinolinecarbonitrile.

  这项发明揭示了一种制备4-氨基-3-喹啉碳腈的过程，包括将胺化合物与氰乙酸和酸催化剂结合以产生氰乙酰胺；将氰乙酰胺与醇溶剂和三烷基正甲酸酯中的一个或多个取代苯胺缩合以产生3-氨基-2-氰基丙烯酰胺；将3-氨基-2-氰基丙烯酰胺与氯化磷在乙腈、丁腈、甲苯或二甲苯中结合，可选地在催化剂存在的情况下以产生4-氨基-3-喹啉碳腈，并且还揭示了一种制备7-氨基噻吩[3,2-b]吡啶-6-碳腈的过程，包括将二取代的3-氨基噻吩与氰乙酰胺和三烷基正甲酸酯在醇溶剂中结合以获得3-氨基-2-氰基丙烯酰胺；将3-氨基-2-氰基丙烯酰胺与氯化磷和乙腈、丁腈、甲苯或二甲苯结合，可选地在催化剂存在的情况下以产生7-氨基噻吩[3,2-b]吡啶-6-碳腈，并且还揭示了一种通过将胺化合物与氰乙酸和肽偶联试剂结合以获得悬浮液；过滤悬浮液以产生氰乙酰胺；将氰乙酰胺与一个或多个取代苯胺、醇溶剂和三乙基正甲酸酯缩合以产生3-氨基-2-氰基丙烯酰胺；将3-氨基-2-氰基丙烯酰胺与氯化磷结合以产生4-氨基-3-喹啉碳腈的制备过程。
• HETEROARYL (ALKYL) DITHIOCARBAMATE COMPOUNDS, PREPARATION METHODS AND USES THEREOF
  申请人：Li Runtao

  公开号：US20130136794A1

  公开（公告）日：2013-05-30

  Heteroaryl(alkyl)dithiocarbamate compounds represented by general formula (I) or their pharmaceutically acceptable salts, their preparing methods, and their uses for preparing antitumor medicines are disclosed, wherein each said substituent is defined as in the description. The compounds are new tyrosine kinase inhibitors useful as an anti-tumor agents, preferably useful in the preparation of medicines for treating breast cancer, liver cancer, non-small cell lung cancer, gastric cancer, colon cancer, leukaemia or nasal cancer.

  通用公式（I）表示的杂环烷基二硫代氨基甲酸酯化合物或其药学上可接受的盐，其制备方法以及用于制备抗肿瘤药物的用途被披露，其中每个取代基如描述中所定义。这些化合物是新的酪氨酸激酶抑制剂，可用作抗肿瘤剂，最好用于制备治疗乳腺癌、肝癌、非小细胞肺癌、胃癌、结肠癌、白血病或鼻癌的药物。
• PROCESS FOR THE MANUFACTURE OF (E)-4-N,N-DIALKYLAMINO CROTONIC ACID IN HX SALT FORM AND USE THEREOF FOR SYNTHESIS OF EGFR TYROSINE KINASE INHIBITORS
  申请人：Boehringer Ingelheim International GmbH

  公开号：US20150183764A1

  公开（公告）日：2015-07-02

  The present invention is directed to an efficient process for the manufacture of (E)-4-N,N-dialkylamino crotonic acid in HX salt form of formula I wherein R 1 and R 2 independently denote C 1-3 -alkyl groups and X − denotes an acid anion, such as the chloride, bromide, tosylate, mesylate or trifluoroacetate anion, with high quality, and a process for synthesis of EGFR tyrosine kinase inhibitors with heterocyclic quinazoline, quinoline or pyrimidopyrimidine core structure, using the acid addition salt I and activated derivatives thereof as intermediates.

  本发明涉及一种高效的(E)-4-N,N-二烷基氨基丙烯酸HX盐的制造工艺，其化学式为I，其中R1和R2独立地表示C1-3烷基基团，X-表示酸根离子，例如氯离子、溴离子、对甲苯磺酸盐离子、甲磺酸盐离子或三氟乙酸盐离子，并且具有高质量。本发明还涉及一种使用酸加成盐I及其活化衍生物作为中间体的含杂环喹唑啉、喹啉或嘧啶基嘧啶类EGFR酪氨酸激酶抑制剂的合成工艺。
• [EN] PROCESS FOR THE MANUFACTURE OF (E)-4-N,N-DIALKYLAMINO CROTONIC ACID IN HX SALT FORM AND USE THEREOF FOR SYNTHESIS OF EGFR TYROSINE KINASE INHIBITORS<br/>[FR] PROCÉDÉ DE FABRICATION D'ACIDE (E)-4-N,N-DIALKYLAMINOCROTONIQUE SOUS FORME DE SEL HX ET SON UTILISATION POUR LA SYNTHÈSE D'INHIBITEURS D'EGFR TYROSINE KINASE
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2015101554A1

  公开（公告）日：2015-07-09

  The present invention is directed to an efficient process for the manufacture of (E)-4-N,N- dialkylamino crotonic acid in HX salt form of formula I, wherein R1 and R2 independently denote C1-3-alkyl groups and Xˉ denotes an acid anion, such as the chloride, bromide, tosylate, mesylate or trifluoroacetate anion, with high quality, and a process for synthesis of EGFR tyrosine kinase inhibitors with heterocyclic quinazoline, quinoline or pyrimidopyrimidine core structure, using the acid addition salt I and activated derivatives thereof as intermediates.

  本发明涉及一种高效的(E)-4-N,N-二烷基氨基巴豆酸HX盐形式的制造工艺，式I中，R1和R2独立表示C1-3烷基基团，Xˉ表示酸根离子，如氯离子、溴离子、tosylate离子、mesylate离子或三氟乙酸根离子，具有高质量，以及一种使用酸加成盐I及其活化衍生物作为中间体的杂环喹唑啉、喹啉或嘧啶并嘧啶酸EGFR酪氨酸激酶抑制剂的合成工艺。