3-acetyl-N-(5,8-dichloro-1,2,3,4-tetrahydro-7-isoquinolinyl)-4-(1-methylethoxy)benzamide hydrochloride | 1198775-31-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-acetyl-N-(5,8-dichloro-1,2,3,4-tetrahydro-7-isoquinolinyl)-4-(1-methylethoxy)benzamide hydrochloride
• 英文别名: SB-406725A；FF38DK5Drb；3-acetyl-N-(5,8-dichloro-1,2,3,4-tetrahydroisoquinolin-7-yl)-4-propan-2-yloxybenzamide;hydrochloride
• CAS: 1198775-31-3
• 化学式: C₂₁H₂₂Cl₂N₂O₃*ClH
• 分子量: 457.784
• InChiKey: ZPPZETVPCOBTOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.43
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3-acetyl-N-(5,8-dichloro-1,2,3,4-tetrahydro-7-isoquinolinyl)-4-(1-methylethoxy)benzamide 在 盐酸 作用下， 以 水 、 异丙醇 为溶剂， 反应 0.5h， 以88%的产率得到3-acetyl-N-(5,8-dichloro-1,2,3,4-tetrahydro-7-isoquinolinyl)-4-(1-methylethoxy)benzamide hydrochloride
  参考文献：
  名称：

  The Development of a New Manufacturing Route to the Novel Anticonvulsant, SB-406725A

  摘要：

  The development of an efficient manufacturing route to 3-acetyl-N-(5,8-dichloro-1,2,3,4-tetrahydro-7-isoquinolinyl)-4-(1-methylethyoxy)-benzamide hydrochloride SB-406725A (1) is described. Title synthesis begins with dichlorination of isoquinoline, followed by nitration using nitronium tetrafluoroborate in sulpholane. Nitroisoquinoline (12) was hydrogenated under pressure using Pt/C. The resultant tetrahydroisoquinoline (13) was selectively coupled with benzoate side chain (15) under base-promoted conditions using sodium hexamethyldisilazane to yield the parent molecule SB406725 (16). SB-406725 was then converted to the HCl salt SB-406725A (1). This process has been successfully demonstrated on a pilot-plant scale to prepare similar to 30 kg of SB-406725A (1).

  DOI：

  10.1021/op9002054