N,N′-(6,6′-(2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis-(methylene)bis(oxy)bis(5-(2-methoxy phenoxy)-2,2′-bipyrimidine-6,4-diyl))bis(4-tert-butylbenzenesulfonamide) | 1448588-52-0

• 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: N,N′-(6,6′-(2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis-(methylene)bis(oxy)bis(5-(2-methoxy phenoxy)-2,2′-bipyrimidine-6,4-diyl))bis(4-tert-butylbenzenesulfonamide)
• 英文别名: 4-tert-butyl-N-[6-[[5-[[6-[(4-tert-butylphenyl)sulfonylamino]-5-(2-methoxyphenoxy)-2-pyrimidin-2-ylpyrimidin-4-yl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]-5-(2-methoxyphenoxy)-2-pyrimidin-2-ylpyrimidin-4-yl]benzenesulfonamide
• CAS: 1448588-52-0
• 化学式: C₅₇H₆₀N₁₀O₁₂S₂
• 分子量: 1141.3
• InChiKey: BIHMZUDPZUMILM-UHFFFAOYSA-N

物化性质

• 密度：
  1.318±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  81
• 可旋转键数：
  22
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  286
• 氢给体数：
  2
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  N,N′-(6,6′-(2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis-(methylene)bis(oxy)bis(5-(2-methoxy phenoxy)-2,2′-bipyrimidine-6,4-diyl))bis(4-tert-butylbenzenesulfonamide) 在 盐酸 、 sodium tetrahydroborate 、 sodium periodate 作用下， 以 甲醇 、 水 、 丙酮 、 乙腈 为溶剂， 生成 波生坦
  参考文献：
  名称：

  A New Efficient Synthetic Process for an Endothelin Receptor Antagonist, Bosentan Monohydrate

  摘要：

  A new and efficient synthetic process for the synthesis of an endothelin receptor antagonist, bosentan monohydrate, involves the coupling of p-tert-butyl-N-(6-chloro-5-(2-methoxy phenoxy)-2,2'-bipyrimidin-4-yl)-benzenesulfonamide (7) with (2,2-dimethyl-1,3-dioxolane-4,5-diyl)dimethanol (14) as a key step. This new process provides desired bosentan monohydrate (1) with better quality and yields. Our new methodology consists of technical innovations/improvements which totally eliminate the probability for the formation of critical impurities such as pyrimidinone 8, dimer impurity 9, and N-alkylated impurity 13 in the final drug substance.

  DOI：

  10.1021/op400100s
• 作为产物：
  描述：

  4-叔丁基苯磺酰胺 在 potassium carbonate 、 sodium hydroxide 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 28.5h， 生成 N,N′-(6,6′-(2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis-(methylene)bis(oxy)bis(5-(2-methoxy phenoxy)-2,2′-bipyrimidine-6,4-diyl))bis(4-tert-butylbenzenesulfonamide)
  参考文献：
  名称：

  A New Efficient Synthetic Process for an Endothelin Receptor Antagonist, Bosentan Monohydrate

  摘要：

  A new and efficient synthetic process for the synthesis of an endothelin receptor antagonist, bosentan monohydrate, involves the coupling of p-tert-butyl-N-(6-chloro-5-(2-methoxy phenoxy)-2,2'-bipyrimidin-4-yl)-benzenesulfonamide (7) with (2,2-dimethyl-1,3-dioxolane-4,5-diyl)dimethanol (14) as a key step. This new process provides desired bosentan monohydrate (1) with better quality and yields. Our new methodology consists of technical innovations/improvements which totally eliminate the probability for the formation of critical impurities such as pyrimidinone 8, dimer impurity 9, and N-alkylated impurity 13 in the final drug substance.

  DOI：

  10.1021/op400100s

文献信息

• Org. Process Res. Dev. 2013, 17, 1021-1026
  作者：

  DOI：——

  日期：——