2-aminopyrrole-3,4-dicarboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-aminopyrrole-3,4-dicarboxamide
• 英文别名: 2-amino-1H-pyrrole-3,4-dicarboxamide
• 化学式: C₆H₈N₄O₂
• 分子量: 168.155
• InChiKey: SYTIQFBZZXXVEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  128
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-aminopyrrole-3,4-dicarboxamide 在 亚硝酸特丁酯 作用下， 以 水 、 溶剂黄146 为溶剂， 以38%的产率得到4-hydroxy-7H-pyrrolo[2,3-d][1,2,3]triazine-5-carboxamide
  参考文献：
  名称：

  Synthesis and Unusual Chemical Reactivity of Certain Novel 4,5-Disubstituted 7-Benzylpyrrolo[2,3-d][1,2,3]triazines

  摘要：

  The fact that only two pyrrolo[2,3-d] [1,2,3]triazines heterocycles had been reported in the literature prompted us to initiate studies designed to provide additional members of this ring system. Initial attempts to prepare additional derivatives of the 7-unsubstituted pyrrolo[2,3-d] [1,2,3]triazin-4-ones were limited by their low chemical reactivity. Subsequently, 7-benzyl-5-carboxamidopyrrololo-,3-d] [1,2,3]triazin-4-one (16) was prepared from diethyl 2-nitropyrrole-3,4,-dicarboxylate via an alkylation, ammonolysis, reduction and intramolecular diazocoupling sequence. Conversion of 16 into 7-benzyl-4-( 1,2,4-triazol-1-yl)pyrrolo [2,3-d] [1,2,3]triazine-5-carbonitrile (17) was accomplished, and nucleophilic displacements of the 4-triazol-1- yl group were studied. Treatment of 17 with NH3/CH3CN gave a mixture of 4-amino-7-benzylpyrrolo [2,3-d] [1,2,3] triazine-5-carbonitrile (19) and 2-amino-1-benzylpyrrole-3,4-dicarbonitrile (21), A mechanism to account for the formation of this mixture is described along with studies on the effect that ammonia concentration and a TFA catalyst have on the product ratio. Compound 19 was converted into the 5-carboxamide and 5-thioamide derivatives of 19.

  DOI：

  10.1021/jo001499i
• 作为产物：
  描述：

  2-氨基-5-甲基硫代-(1h)-吡咯-3,4-二羧酰胺 在 镍 异丙醇 作用下， 以 异丙醇 为溶剂， 反应 24.0h， 以to afford first crop of 2-amino-pyrrole-3,4-dicarboxamide (70b) 2.64 g (22%) as a purple solid的产率得到2-aminopyrrole-3,4-dicarboxamide
  参考文献：
  名称：

  Heterocyclic Compounds as Janus Kinase Inhibitors

  摘要：

  本发明提供了以下式子（I）的化合物或其盐，如本文所述。本发明还提供了包含式子（I）化合物的制药组合物，制备式子（I）化合物的方法，用于制备式子（I）化合物的中间体以及使用式子（I）化合物抑制免疫反应或治疗癌症或血液恶性肿瘤的治疗方法。

  公开号：

  US20120149662A1

文献信息

• [EN] HETEROCYCLIC COMPOUNDS AS JANUS KINASE INHIBITORS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES EN TANT QU'INHIBITEURS DE JANUS KINASE
  申请人：BIOCRYST PHARM INC

  公开号：WO2011031554A3

  公开（公告）日：2011-09-15
• HETEROCYCLIC COMPOUNDS AS JANUS KINASE INHIBITORS
  申请人：BIOCRYST PHARMACEUTICALS, INC.

  公开号：EP2470537A2

  公开（公告）日：2012-07-04