4-hydroxy-7-{2-[(2-{[3-(2-phenylethoxy)propyl]sulfonyl}ethyl)amino]ethyl}-1,3-benzothiazol-2(3H)-one | 154189-61-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 4-hydroxy-7-{2-[(2-{[3-(2-phenylethoxy)propyl]sulfonyl}ethyl)amino]ethyl}-1,3-benzothiazol-2(3H)-one
• 英文别名: N-[2-[4-Hydroxy-2-oxo-3H-1,3-benzothiazole-7-yl]ethyl]-2-[3-[2-phenylethoxy]propylsulphonyl]acetamide；N-[2-(4-hydroxy-2-oxo-3H-1,3-benzothiazol-7-yl)ethyl]-2-[3-(2-phenylethoxy)propylsulfonyl]acetamide
• CAS: 154189-61-4
• 化学式: C₂₂H₂₆N₂O₆S₂
• 分子量: 478.59
• InChiKey: AKIPFTBUUKVCSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  156
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-hydroxy-7-{2-[(2-{[3-(2-phenylethoxy)propyl]sulfonyl}ethyl)amino]ethyl}-1,3-benzothiazol-2(3H)-one 以31的产率得到盐酸西贝奈迪
  参考文献：
  名称：

  J. Med. Chem. 1998, 41, 4915-4917

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(4-甲氧苯基)乙胺 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 甲烷磺酸 、 copper(II) choride dihydrate 、 硫酸 、 palladium on activated charcoal 、 氢溴酸 、 氢气 、 硝酸 、 sodium methylate 、 乙酸酐 、 溶剂黄146 、 三乙胺 、 N,N'-羰基二咪唑 、 copper(l) chloride 、 sodium hydroxide 、 sodium nitrite 作用下， 以 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 125.0 ℃ 、300.01 kPa 条件下， 反应 49.0h， 生成 4-hydroxy-7-{2-[(2-{[3-(2-phenylethoxy)propyl]sulfonyl}ethyl)amino]ethyl}-1,3-benzothiazol-2(3H)-one
  参考文献：
  名称：

  Development of a Manufacturing Process for Sibenadet Hydrochloride, the Active Ingredient of Viozan

  摘要：

  A process for commercial manufacture of the dual D-2-beta(2) receptor agonist sibenadet hydrochloride has been developed. The process relies upon introduction of operationally simple chemistry at the final stages where two key intermediates are reacted to assemble the final molecule, isolated by crystallization. A nine-stage sequence for synthesis of the key amine hydrochloride intermediate was developed, and modifications to the original process are described. Major strategic improvements were made in definition of the final route to the "side chain" precursor molecule, the second key intermediate, hinging around a thiyl radical addition and subsequent high-yielding telescoped processes for synthesis of this highly crystalline benzoate ester. Development of these chemistries is discussed, together with some issues surrounding definition of the final validated commercial processes.

  DOI：

  10.1021/op049953y

文献信息

• 7-(2-AMINOETHYL)-BENZOTHIAZOLONES
  申请人：Astra Pharmaceuticals Limited

  公开号：EP0649418B1

  公开（公告）日：1998-10-28
• US5648370A
  申请人：——

  公开号：US5648370A

  公开（公告）日：1997-07-15
• Development of a Manufacturing Process for Sibenadet Hydrochloride, the Active Ingredient of Viozan
  作者：Melvyn E. Giles、Colin Thomson、Stephen C. Eyley、Andrea J. Cole、Christopher J. Goodwin、Paul A. Hurved、Andrew J. G. Morlin、James Tornos、Stéphanie Atkinson、Cecelia Just、Janet C. Dean、John T. Singleton、Andrew J. Longton、Ian Woodland、Andrew Teasdale、Björn Gregertsen、Howard Else、Mandip S. Athwal、Stephen Tatterton、Jason M. Knott、Nicola Thompson、Stephen J. Smith

  DOI：10.1021/op049953y

  日期：2004.7.1

  A process for commercial manufacture of the dual D-2-beta(2) receptor agonist sibenadet hydrochloride has been developed. The process relies upon introduction of operationally simple chemistry at the final stages where two key intermediates are reacted to assemble the final molecule, isolated by crystallization. A nine-stage sequence for synthesis of the key amine hydrochloride intermediate was developed, and modifications to the original process are described. Major strategic improvements were made in definition of the final route to the "side chain" precursor molecule, the second key intermediate, hinging around a thiyl radical addition and subsequent high-yielding telescoped processes for synthesis of this highly crystalline benzoate ester. Development of these chemistries is discussed, together with some issues surrounding definition of the final validated commercial processes.
• J. Med. Chem. 1998, 41, 4915-4917
  作者：

  DOI：——

  日期：——