methyl 5-(acetylamino)-1H-1,2,4-triazole-3-carboxylate

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: methyl 5-(acetylamino)-1H-1,2,4-triazole-3-carboxylate
• 英文别名: 5-Acetylamino-1H-[1,2,4]triazole-3-carboxylic acid methyl ester；methyl 3-acetamido-1H-1,2,4-triazole-5-carboxylate
• 化学式: C₆H₈N₄O₃
• mdl: MFCD00297289
• 分子量: 184.155
• InChiKey: BQKSBCYRDTWIPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  97
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 5-(acetylamino)-1H-1,2,4-triazole-3-carboxylate 、 氢氧化锂 在 水 作用下， 以 Methanol tetrahydrofuran water 为溶剂， 反应 1.0h， 以to afford the titled compound as a white solid (413 mg), which的产率得到3-乙酰氨基-1H-1,2,4-三氮唑-5-甲酸
  参考文献：
  名称：

  PYRAZOLO[1,5-a]PYRIMIDINE COMPOUNDS AS mTOR INHIBITORS

  摘要：

  本发明提供了式（I）的吡唑吡咯啉化合物：其中L、T、Z、U、V、W、R3、R6、R7、R8和m如本文所定义，并且这些吡唑吡咯啉化合物的药物可接受的盐。这些吡唑吡咯啉化合物在治疗癌症和其他mTOR失调的疾病或疾病中具有用处。

  公开号：

  US20120322791A1
• 作为产物：
  描述：

  5-氨基-1H-1,2,4-三氮唑-3-羧酸甲酯 、 乙酸酐 反应 0.5h， 以98%的产率得到methyl 5-(acetylamino)-1H-1,2,4-triazole-3-carboxylate
  参考文献：
  名称：

  Synthesis, Structure and Properties of N-Acetylated Derivatives of Methyl 5-Amino-1H-[1,2,4]triazole-3-carboxylate

  摘要：

  ino)-1H-[1,2,4]triazole-3-carboxylate (6)。

  DOI：

  10.1248/cpb.52.192

文献信息

• [EN] PYRAZOLO[1,5-a]PYRIMIDINE COMPOUNDS AS mTOR INHIBITORS<br/>[FR] COMPOSÉS PYRAZOLO[1,5-A]PYRIMIDINES EN TANT QU'INHIBITEURS DE MTOR
  申请人：MERCK SHARP & DOHME

  公开号：WO2011090935A1

  公开（公告）日：2011-07-28

  The present invention provides Pyrazolopyrimidine Compounds of Formula (I): (I) wherein L, T, Z, U, V, W, R3, R6, R7, R8, and m are as defined herein, and pharmaceutically acceptable salts of such Pyrazolopyrimidine Compounds. The Pyrazolopyrimidine Compounds are useful in the treatment of cancer and other diseases or disorders wherein mTOR is deregulated.

  本发明提供了式(I)的吡唑吡咯嘧啶化合物：其中L、T、Z、U、V、W、R3、R6、R7、R8和m如本文所定义，并且提供了这些吡唑吡咯嘧啶化合物的药用可接受的盐。这些吡唑吡咯嘧啶化合物在治疗癌症和其他疾病或紊乱中mTOR被破坏时是有用的。
• PYRAZOLO[1,5-a]PYRIMIDINE COMPOUNDS AS mTOR INHIBITORS
  申请人：Siddiqui M. Arshad

  公开号：US20120322791A1

  公开（公告）日：2012-12-20

  The present invention provides Pyrazolopyrimidine Compounds of Formula (I): wherein L, T, Z, U, V, W, R 3 , R 6 , R 7 , R 8 , and m are as defined herein, and pharmaceutically acceptable salts of such Pyrazolopyrimidine Compounds. The Pyrazolopyrimidine Compounds are useful in the treatment of cancer and other diseases or disorders wherein mTOR is deregulated.

  本发明提供了式（I）的吡唑吡咯啉化合物：其中L、T、Z、U、V、W、R3、R6、R7、R8和m如本文所定义，并且这些吡唑吡咯啉化合物的药物可接受的盐。这些吡唑吡咯啉化合物在治疗癌症和其他mTOR失调的疾病或疾病中具有用处。
• US9227971B2
  申请人：——

  公开号：US9227971B2

  公开（公告）日：2016-01-05
• Synthesis, Structure and Properties of N-Acetylated Derivatives of Methyl 5-Amino-1H-[1,2,4]triazole-3-carboxylate
  作者：Anetta Dżygiel、Barbara Rzeszotarska、Elżbieta Masiukiewicz、Piotr Cmoch、Bohdan Kamieński

  DOI：10.1248/cpb.52.192

  日期：——

  Methyl 5-amino-1H-[1,2,4]triazole-3-carboxylate hydrochloride (1) and free ester (2) were obtained and 2 was reacted with Ac2O to give the acetylated products 3—6. Compounds 1—6 were studied using HPLC, GC-MS, FTIR and multinuclear NMR spectroscopy, including the cross-polarisation magic angle spinning (CPMAS) technique. The results of the acetylation of 2 were compared to those of the acetylation of 5-amino-1H-[1,2,4]triazole, and for 2 a significant decrease in the susceptibility to acetylation was found. The reaction of 2 with Ac2O at 20 °C, regardless of the amount and the concentration of the latter, including neat Ac2O, proceeds fully regioselectively and leads to one product: methyl 1-acetyl-5-amino-1H-[1,2,4]triazole-3-carboxylate (3). In sharp contrast to 5-amino-1H-[1,2,4]triazole, neither an additional monoacetylated isomer, whether annular or exocyclic, nor any diacetylated derivative could be detected. The diacetylation of 2 requires the process to be carried out in neat boiling Ac2O and, as in the case of 5-amino-1H-[1,2,4]triazole, gives two diacetylated isomers. These are methyl 1-acetyl-3-(acetylamino)-1H-[1,2,4]triazole-5-carboxylate (4) and 1-acetyl-5-(acetylamino)-1H-[1,2,4]triazole-3-carboxylate (5). Hypothetical pathways of their formation have been suggested. A mixture of 4 and 5 upon hydrolysis of the ring acetyl group gives the monoacetylated derivative methyl 5-(acetylamino)-1H-[1,2,4]triazole-3-carboxylate (6). The spectroscopic, structural and conformational characteristics of compounds 1—6 have been given and methods for their preparation have been provided.

  ino)-1H-[1,2,4]triazole-3-carboxylate (6)。
• Pyrazolo[1,5-a]pyrimidine compounds as mTOR inhibitors
  申请人：Siddiqui M. Arshad

  公开号：US09227971B2

  公开（公告）日：2016-01-05

  The present invention provides Pyrazolopyrimidine Compounds of Formula (I): wherein L, T, Z, U, V, W, R3, R6, R7, R8, and m are as defined herein, and pharmaceutically acceptable salts of such Pyrazolopyrimidine Compounds. The Pyrazolopyrimidine Compounds are useful in the treatment of cancer and other diseases or disorders wherein mTOR is deregulated.

  本发明提供了式（I）的吡唑吡咯啉化合物，其中L、T、Z、U、V、W、R3、R6、R7、R8和m的定义如本文所述，并且这些吡唑吡咯啉化合物的药学上可接受的盐。这些吡唑吡咯啉化合物可用于治疗癌症和其他mTOR失调相关的疾病或疾病。