5-[3-(3-hydroxyphenoxy)azetidin-1-yl]-5-methyl-2,2-diphenylhexanenitrile | 931409-66-4

• 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: 5-[3-(3-hydroxyphenoxy)azetidin-1-yl]-5-methyl-2,2-diphenylhexanenitrile
• 英文别名: 5-[3-(3-Hydroxyphenoxy)azetidin-1-yl]-5-methyl-2,2-diphenyl-hexanenitrile
• CAS: 931409-66-4
• 化学式: C₂₈H₃₀N₂O₂
• 分子量: 426.558
• InChiKey: BGMKZJYUBNKRRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  56.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-[3-(3-hydroxyphenoxy)azetidin-1-yl]-5-methyl-2,2-diphenylhexanenitrile 在 potassium hydroxide 、 盐酸 、 水 作用下， 以 2-甲基-2-丁醇 、 tert-butylmethyl ether 为溶剂， 反应 43.0h， 以76%的产率得到5-[3-(3-hydroxyphenoxy)azetidin-1-yl]-5-methyl-2,2 diphenyl hexanamide hydrochloride
  参考文献：
  名称：

  Development of a Scaleable Synthesis of a Geminal Dimethyl Tertiary Amine as an Inhaled Muscarinic Antagonist for the Treatment of COPD

  摘要：

  An efficient and scalable process for the synthesis of muscarinic antagonist, PF-3635659 1, is described, illustrating redesign of an analogue-targeted synthesis which contained a scale-limiting rhodium-activated C H amination step. The final route includes a reproducible modified Bouveault reaction which has not previously been reported on a substrate of this complexity, or on such a scale with over 5 kg of the requisite gem-dimethylamine prepared via this methodology.

  DOI：

  10.1021/op200233r
• 作为产物：
  描述：

  1-benzhydryl-3-(3-methoxyphenoxy)azetidine 在 4-二甲氨基吡啶 、 甲烷磺酸 、 20 wt.% Pd(OH)2 on activated carbon 、 氢气 、 氯化锆(IV) 作用下， 以 四氢呋喃 、 乙醇 、 丙腈 为溶剂， -5.0~30.0 ℃ 、413.7 kPa 条件下， 反应 144.67h， 生成 5-[3-(3-hydroxyphenoxy)azetidin-1-yl]-5-methyl-2,2-diphenylhexanenitrile
  参考文献：
  名称：

  Development of a Scaleable Synthesis of a Geminal Dimethyl Tertiary Amine as an Inhaled Muscarinic Antagonist for the Treatment of COPD

  摘要：

  An efficient and scalable process for the synthesis of muscarinic antagonist, PF-3635659 1, is described, illustrating redesign of an analogue-targeted synthesis which contained a scale-limiting rhodium-activated C H amination step. The final route includes a reproducible modified Bouveault reaction which has not previously been reported on a substrate of this complexity, or on such a scale with over 5 kg of the requisite gem-dimethylamine prepared via this methodology.

  DOI：

  10.1021/op200233r

文献信息

• [EN] METHODS AND INTERMEDIATES FOR PREPARING HYDROCHLORIDE SALT OF 5-[3-(3-HYDROXYPHENOXY)AZETIDIN-1-YL]-5-METHYL-2,2-DIPHENYLHEXANAMIDE<br/>[FR] PROCÉDÉS ET INTERMÉDIAIRES POUR LA PRÉPARATION DE SEL DE CHLORHYDRATE DE 5- [3-(3-HYDROXYPHÉNOXY)AZÉTIDINE-1-YL]-5-MÉTHYL-2,2-DIPHÉNYLHEXANAMIDE
  申请人：MYLAN LABORATORIES LTD

  公开号：WO2020261160A1

  公开（公告）日：2020-12-30

  Methods for providing a carboxamide compound and intermediates used in the preparation of the carboxamide compound are provided. The methods include reacting 5-[3-(3-hydroxyphenoxy)azetidin-1-yl]-5-methyl-2,2-diphenylhexanenitrile benzoate with a reagent and hydrochloric acid to form the carboxamide compound including 5-[3-(3-hydroxyphenoxy)azetidin-1-yl]-5-methyl-2,2-diphenylhexanamide hydrochloride.

  本发明提供了一种提供羧酰胺化合物及用于制备该羧酰胺化合物的中间体的方法。该方法包括使用试剂和盐酸反应5-[3-(3-羟基苯氧基)氮杂-1-基]-5-甲基-2,2-联苯己腈苯酸酯，以形成羧酰胺化合物，其中包括5-[3-(3-羟基苯氧基)氮杂-1-基]-5-甲基-2,2-联苯己酰胺盐酸盐。
• Carboxamide derivatives as muscarinic receptor antagonists
  申请人：Glossop Alan Paul

  公开号：US20070105831A1

  公开（公告）日：2007-05-10

  The invention relates to compounds of formula processes and intermediates for their preparation, their use as muscarinic antagonists and pharmaceutical composition containing them.

  本发明涉及具有下列公式的化合物、其制备方法和中间体，以及包含它们的抗胆碱能药物组合物。
• Carboxamide Derivatives As Muscarinic Receptor Antagonists
  申请人：Glossop Paul Alan

  公开号：US20100029720A1

  公开（公告）日：2010-02-04

  The invention relates to compounds of formula processes and intermediates for their preparation, their use as muscarinic antagonists and pharmaceutical composition containing them.

  本发明涉及具有以下式的化合物，以及制备它们的过程和中间体，它们作为毒蕈碱受体拮抗剂的用途和包含它们的制药组合物。
• Hydrochloride salt of 5-[3-(3-hydroxyphenoxy) azetidin-1-yl]-5-methyl-2,2-diphenylhexanamide
  申请人：Glossop Paul Alan

  公开号：US20100113409A1

  公开（公告）日：2010-05-06

  This invention relates to the hydrochloride salt of 5-[3-3-hydroxyphenoxy)azetidin-1-yl]-5-methyl-2,2-diphenyl-hexanamide or derived form thereof and its use as a medicament.

  本发明涉及5-[3-3-羟基苯氧基)氮杂环己酰胺-5-甲基-2,2-二苯基-或其衍生物的盐，并作为药物使用。
• Hydrochloride salt of 5-[3-(3-hydroxyphenoxy)azetidin-1-yl]-5-methyl-2,2-diphenylhexanamide
  申请人：Pfizer Limited

  公开号：US08263583B2

  公开（公告）日：2012-09-11

  This invention relates to the hydrochloride salt of 5-[3-3-hydroxyphenoxy)azetidin-1-yl]-5-methyl-2,2-diphenyl-hexanamide or derived form thereof and its use as a medicament.

  本发明涉及5-[3-3-羟基苯氧基)氮杂环己烷-1-基]-5-甲基-2,2-二苯基己酰胺或其衍生物的盐酸盐及其作为药物的用途。