7-benzyl-4-(1,2,4-triazol-1-yl)pyrrolo[2,3-d][1,2,3]triazine-5-carbonitrile | 244028-92-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并三嗪类
• 英文名称: 7-benzyl-4-(1,2,4-triazol-1-yl)pyrrolo[2,3-d][1,2,3]triazine-5-carbonitrile
• 英文别名: 7-benzyl-4-(triazol-1-yl)pyrrolo[2,3-d][1,2,3]triazin-5-carbonitrile；7-benzyl-4-(1H-1,2,4-triazol-1-yl)-7H-pyrrolo[2,3-d][1,2,3]triazine-5-carbonitrile；7-benzyl-4-(1,2,4-triazol-1-yl)pyrrolo[2,3-d]triazine-5-carbonitrile
• CAS: 244028-92-0
• 化学式: C₁₅H₁₀N₈
• 分子量: 302.298
• InChiKey: UJFBCFPQIMZKFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  98.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-benzyl-4-(1,2,4-triazol-1-yl)pyrrolo[2,3-d][1,2,3]triazine-5-carbonitrile 在 四(三苯基膦)钯 苄基三乙基氯化铵 、 水 、 potassium carbonate 、 N,N-二甲基苯胺 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 乙二醇二甲醚 、 乙腈 为溶剂， 反应 21.0h， 生成 7-benzyl-4-(1-(1-ethoxyethyl)-1H-pyrazol-4-yl)-7H-pyrrolo[2,3-d][1,2,3]triazine-5-carbonitrile
  参考文献：
  名称：

  [EN] HETEROCYCLIC COMPOUNDS AS JANUS KINASE INHIBITORS
  [FR] COMPOSÉS HÉTÉROCYCLIQUES EN TANT QU'INHIBITEURS DE JANUS KINASE

  摘要：

  公开号：

  WO2011031554A3
• 作为产物：
  描述：

  2-amino-1-benzylpyrrole-3,4-dicarboxamide 在 盐酸 、 三乙胺 、 sodium nitrite 、 三氯氧磷 作用下， 以 水 为溶剂， 反应 4.5h， 生成 7-benzyl-4-(1,2,4-triazol-1-yl)pyrrolo[2,3-d][1,2,3]triazine-5-carbonitrile
  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

文献信息

• An Unprecedented Nitrogen Elimination Reaction:  Mechanistic Studies Using ¹⁵N-Labeled 4-Amino-7-benzylpyrrolo[2,3-<i>d</i>][1,2,3]triazine-5-carbonitrile
  作者：Michael T. Migawa、Leroy B. Townsend

  DOI：10.1021/ol990006x

  日期：1999.8.1

  [formula: see text] In the course of our work on novel pyrrolo[2,3-d][1,2,3]triazines we have discovered that 1 undergoes an elimination of nitrogen at 250 degrees C to give 2. We have conducted 15N labeling studies that establish that the loss of N-2 and N-3 from 1 had occurred rather than N-1 and N-2, presumably via a retro Diels-Alder reaction of the imino tautomer 7. This study provides an alternative

  [公式：参见文本]在我们研究新型吡咯并[2,3-d] [1,2,3]三嗪的过程中，我们发现1在250℃时会消除氮，从而得到2。进行了15N标记研究，确定发生了1的N-2和N-3的损失，而不是N-1和N-2的损失，大概是通过亚氨基互变异构体7的Diels-Alder逆反应。常见的机理涉及通过短暂形成重氮化合物而损失N-1和N-2，重氮化合物是由4-氨基或4-氧取代的1,2,3-三嗪与碳环或杂环稠合生成的。
• Heterocyclic Compounds as Janus Kinase Inhibitors
  申请人：Babu Yarlagadda S.

  公开号：US20120149662A1

  公开（公告）日：2012-06-14

  The invention provides compounds of formula (I): or a salt thereof as described herein. The invention also provides pharmaceutical compositions comprising a compound of formula (I), processes for preparing compounds of formula (I), intermediates useful for preparing compounds of formula (I) and therapeutic methods for suppressing an immune response or treating cancer or a hematologic malignancy using compounds of formula (I).

  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。
• HETEROCYCLIC COMPOUNDS AS JANUS KINASE INHIBITORS
  申请人：BIOCRYST PHARMACEUTICALS, INC.

  公开号：EP2470537A2

  公开（公告）日：2012-07-04
• [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
• Synthesis and Unusual Chemical Reactivity of Certain Novel 4,5-Disubstituted 7-Benzylpyrrolo[2,3-<i>d</i>][1,2,3]triazines
  作者：Michael T. Migawa、Leroy B. Townsend

  DOI：10.1021/jo001499i

  日期：2001.7.1

  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.