2-(2-aminopropan-2-yl)-N-benzyl-1,6-dihydro-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide | 1403457-41-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-(2-aminopropan-2-yl)-N-benzyl-1,6-dihydro-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide
• 英文别名: 2-(2-aminopropan-2-yl)-N-benzyl-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide
• CAS: 1403457-41-9
• 化学式: C₁₆H₂₀N₄O₃
• 分子量: 316.36
• InChiKey: VJZCTIRKVVZJEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-甲基-1,3,4-噁二唑-2-羰酰氯 、 2-(2-aminopropan-2-yl)-N-benzyl-1,6-dihydro-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide 在 N-甲基吗啉 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 1.0h， 以13 g的产率得到雷特格韦相关化合物E(USP)
  参考文献：
  名称：

  Identification, Synthesis, and Strategy For Minimization of Potential Impurities Observed In Raltegravir Potassium Drug Substance

  摘要：

  Multiple sources of anticipated degradation and process impurities of raltegravir potassium drug substance observed during the laboratory optimization and later during its bulk synthesis are described in this article. The impurities were monitored by UPLC, and their structures are tentatively assigned on the basis of fragmentation patterns in LC-MS and NMR spectroscopy. Most of the impurities are synthesized, and their assigned constitutions were confirmed by co-injection in UPLC. In addition to the formation, synthesis, and characterization, strategy for minimizing these impurities to the level accepted by ICH is also described. We feel that our study will be helpful to the generic industry for obtaining chemically pure raltegravir potassium.

  DOI：

  10.1021/op300077m
• 作为产物：
  描述：

  在 甲烷磺酸 、 10% Pd/C 、 氢气 作用下， 以 甲醇 为溶剂， 50.0~55.0 ℃ 、200.0 kPa 条件下， 以82%的产率得到2-(2-aminopropan-2-yl)-N-benzyl-1,6-dihydro-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide
  参考文献：
  名称：

  Identification, Synthesis, and Strategy For Minimization of Potential Impurities Observed In Raltegravir Potassium Drug Substance

  摘要：

  Multiple sources of anticipated degradation and process impurities of raltegravir potassium drug substance observed during the laboratory optimization and later during its bulk synthesis are described in this article. The impurities were monitored by UPLC, and their structures are tentatively assigned on the basis of fragmentation patterns in LC-MS and NMR spectroscopy. Most of the impurities are synthesized, and their assigned constitutions were confirmed by co-injection in UPLC. In addition to the formation, synthesis, and characterization, strategy for minimizing these impurities to the level accepted by ICH is also described. We feel that our study will be helpful to the generic industry for obtaining chemically pure raltegravir potassium.

  DOI：

  10.1021/op300077m