5-(5-(2-(((tert-butoxycarbonyl)amino)methyl)-5-fluorobenzamido)-N-methylpentylsulfonamido)-8-hydroxy-1,6-naphthyridine-7-carboxylic acid | 1480815-60-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 5-(5-(2-(((tert-butoxycarbonyl)amino)methyl)-5-fluorobenzamido)-N-methylpentylsulfonamido)-8-hydroxy-1,6-naphthyridine-7-carboxylic acid
• CAS: 1480815-60-8
• 化学式: C₂₈H₃₄FN₅O₈S
• 分子量: 619.671
• InChiKey: AETZBNVHCNQIQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  43.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  188.12
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  5-(5-(2-(((tert-butoxycarbonyl)amino)methyl)-5-fluorobenzamido)-N-methylpentylsulfonamido)-8-hydroxy-1,6-naphthyridine-7-carboxylic acid 在 盐酸 、 1-丙基磷酸酐 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 6H-5,22-iminopyrido[3,2-k][8,2,9,16]-benzothiatriazacyclononadecine-14,21-dione,16-fluoro-8,9,10,11,12,13,19,20-octahydro-23-hydroxy-6-methyl-7,7-dioxide
  参考文献：
  名称：

  Copper-Catalyzed C–N Coupling in the Synthesis of Integrase Inhibitors of Immunodeficiency Viruses

  摘要：

  This contribution describes the total synthesis of a complex macrocyclic integrase inhibitor, a key enzyme involved in the infection process of various immunodeficiency viruses. The key transformation of the synthetic strategy was the selective C-N coupling of a sulfonamide to a heteroaryl bromide in the presence of potentially competing amide and carbamate functionalities. The transformation was accomplished with CuI catalysis using bypiridine as the ligand in the presence of base and enabled a convergent approach to the target molecule.

  DOI：

  10.1021/op400228z
• 作为产物：
  描述：

  methyl 2-((tert-butoxycarbonylamino)methyl)-5-fluorobenzoate 在 2,2'-联吡啶 、 copper(l) iodide 、 水 、 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 5-(5-(2-(((tert-butoxycarbonyl)amino)methyl)-5-fluorobenzamido)-N-methylpentylsulfonamido)-8-hydroxy-1,6-naphthyridine-7-carboxylic acid
  参考文献：
  名称：

  Copper-Catalyzed C–N Coupling in the Synthesis of Integrase Inhibitors of Immunodeficiency Viruses

  摘要：

  This contribution describes the total synthesis of a complex macrocyclic integrase inhibitor, a key enzyme involved in the infection process of various immunodeficiency viruses. The key transformation of the synthetic strategy was the selective C-N coupling of a sulfonamide to a heteroaryl bromide in the presence of potentially competing amide and carbamate functionalities. The transformation was accomplished with CuI catalysis using bypiridine as the ligand in the presence of base and enabled a convergent approach to the target molecule.

  DOI：

  10.1021/op400228z