2-(4-aminophenyl)-N-[(2R)-2-hydroxy-2-pyridin-3-ylethyl]acetamide | 211371-13-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-aminophenyl)-N-[(2R)-2-hydroxy-2-pyridin-3-ylethyl]acetamide
• CAS: 211371-13-0
• 化学式: C₁₅H₁₇N₃O₂
• 分子量: 271.319
• InChiKey: KLIXNGWWOKUAJU-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  88.2
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-aminophenyl)-N-[(2R)-2-hydroxy-2-pyridin-3-ylethyl]acetamide 在 吡啶 、 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 11.0h， 生成 (R)-N-{4-[2-(2-hydroxy-2-pyridin-3-yl-ethylamino)-ethyl]-phenyl}-4-[4-(4-trifluoromethyl-phenyl)-thiazol-2-yl]-benzenesulfonamide
  参考文献：
  名称：

  实际路由到triarylsulfonyl氯化物中间体β的3肾上腺素能受体激动剂

  摘要：

  甲β 3肾上腺素能受体激动剂经汇集合成在高产率和高纯度的多千克规模制备。该合成中的关键中间体是芳基噻唑基苯磺酰氯。该磺酰氯的三芳基链段通过α-卤代酮和硫代苯甲酰胺前体的偶合在噻唑环上组装（Hantzsch合成）。开发和评估了引入对-磺酰氯部分的三种策略。发现磺化/氯化和重氮化/氯磺酰化途径是最有效的。

  DOI：

  10.1016/s0040-4020(03)00018-8
• 作为产物：
  描述：

  3-乙酰基吡啶 在 palladium on activated charcoal 盐酸 、 ammonium hydroxide 、 yeast Candida sorbophilia 、 盐酸羟胺 、 potassium ethoxide 、 氢气 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 水 为溶剂， 28.0~40.0 ℃ 、137.9 kPa 条件下， 反应 51.0h， 生成 2-(4-aminophenyl)-N-[(2R)-2-hydroxy-2-pyridin-3-ylethyl]acetamide
  参考文献：
  名称：

  Practical chemoenzymatic synthesis of a 3-pyridylethanolamino β3 adrenergic receptor agonist

  摘要：

  A chemoenzymatic synthesis of beta(3) agonist 1 suitable for large scale preparation is described. The key chiral 3-pyridylethanolamine intermediate (R)-7 was prepared via an improved Neber rearrangement and a yeast-mediated asymmetric reduction. The tetrazolone fragment of the molecule was constructed via a dipolar cycloaddition between 1-(cyclopentyl)-3-propylazide and p-chlorosulfonyl phenylisocyanate. Sulfonamide coupling of these two intermediates under Shotten-Baumann conditions, followed by a borane reduction of the amide afforded 1 in 20-32% overall yield from 3-acetylpyridine, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01353-2

文献信息

• Practical chemoenzymatic synthesis of a 3-pyridylethanolamino β3 adrenergic receptor agonist
  作者：John Y.L Chung、Guo-Jie Ho、Michel Chartrain、Chris Roberge、Dalian Zhao、John Leazer、Roger Farr、Michael Robbins、Kateeta Emerson、David J Mathre、James M McNamara、David L Hughes、Edward J.J Grabowski、Paul J Reider

  DOI：10.1016/s0040-4039(99)01353-2

  日期：1999.9

  A chemoenzymatic synthesis of beta(3) agonist 1 suitable for large scale preparation is described. The key chiral 3-pyridylethanolamine intermediate (R)-7 was prepared via an improved Neber rearrangement and a yeast-mediated asymmetric reduction. The tetrazolone fragment of the molecule was constructed via a dipolar cycloaddition between 1-(cyclopentyl)-3-propylazide and p-chlorosulfonyl phenylisocyanate. Sulfonamide coupling of these two intermediates under Shotten-Baumann conditions, followed by a borane reduction of the amide afforded 1 in 20-32% overall yield from 3-acetylpyridine, (C) 1999 Elsevier Science Ltd. All rights reserved.
• Practical routes to the triarylsulfonyl chloride intermediate of a β3 adrenergic receptor agonist
  作者：Norihiro Ikemoto、Jinchu Liu、Karel M.J Brands、James M McNamara、Paul J Reider

  DOI：10.1016/s0040-4020(03)00018-8

  日期：2003.2

  was an arylthiazolylbenzenesulfonyl chloride. The triaryl segment of this sulfonyl chloride was assembled at the thiazole ring via coupling of α-haloketone and thiobenzamide precursors (Hantzsch synthesis). Three strategies for introducing the para-sulfonyl chloride moiety were developed and evaluated. The sulfonation/chlorination and diazotization/chlorosulfonylation routes were found the most efficient

  甲β 3肾上腺素能受体激动剂经汇集合成在高产率和高纯度的多千克规模制备。该合成中的关键中间体是芳基噻唑基苯磺酰氯。该磺酰氯的三芳基链段通过α-卤代酮和硫代苯甲酰胺前体的偶合在噻唑环上组装（Hantzsch合成）。开发和评估了引入对-磺酰氯部分的三种策略。发现磺化/氯化和重氮化/氯磺酰化途径是最有效的。