4-[4-(3-trifluoromethylphenyl)-1H-imidazol-2-yl]piperidine | 1082950-12-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-[4-(3-trifluoromethylphenyl)-1H-imidazol-2-yl]piperidine
• 英文别名: 4-(4-(3-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)piperidine；4-[5-[3-(trifluoromethyl)phenyl]-1H-imidazol-2-yl]piperidine
• CAS: 1082950-12-6
• 化学式: C₁₅H₁₆F₃N₃
• 分子量: 295.307
• InChiKey: ROGYJTCGEPAVSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  40.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-溴-4-氯吡啶 、 4-[4-(3-trifluoromethylphenyl)-1H-imidazol-2-yl]piperidine 在 N,N-二异丙基乙胺 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 4.0h， 以64%的产率得到3-bromo-4-(4-{4-[3-(trifluoromethyl)phenyl]-1H-imidazol-2-yl}piperidin-1-yl)pyridine
  参考文献：
  名称：

  [EN] NOVEL IMIDAZOLE AMINES AS MODULATORS OF KINASE ACTIVITY
  [FR] NOUVEAUX IMIDAZOLES AMINES EN TANT QUE MODULATEURS D'ACTIVITÉ KINASE

  摘要：

  该发明提供了根据式（I）和式（II）的新型咪唑胺化合物，其制备和用于治疗高增殖性疾病，如癌症。

  公开号：

  WO2013040059A1
• 作为产物：
  描述：

  4-[2-oxo-2-(3-trifluoromethyl-phenyl)-ethylcarbamoyl]piperidine-1-carboxylic acid tert-butyl ester 在 乙醇 、 氯化铵 作用下， 120.0~160.0 ℃ 、1.38 MPa 条件下， 反应 16.0h， 以75%的产率得到4-[4-(3-trifluoromethylphenyl)-1H-imidazol-2-yl]piperidine
  参考文献：
  名称：

  WO2008/140947

  摘要：

  公开号：

文献信息

• P70 S6 kinase inhibitors
  申请人：Eli Lilly and Company

  公开号：US08093383B2

  公开（公告）日：2012-01-10

  The present invention provides p70 S6 kinase inhibitors of the formula: pharmaceutical formulations comprising them, and methods for their use.

  本发明提供了式为p70 S6激酶抑制剂的制剂：包括它们的药物制剂，以及使用它们的方法。
• P70 S6 KINASE INHIBITORS
  申请人：Dally Robert Dean

  公开号：US20120071490A1

  公开（公告）日：2012-03-22

  The present invention provides p70 S6 kinase inhibitors of the formula: pharmaceutical formulations comprising them, and methods for their use.

  本发明提供了公式为：p70 S6激酶抑制剂的制剂，以及包含它们的药物制剂和使用它们的方法。
• Imidazole amines as modulators of kinase activity
  申请人：Lan Ruoxi

  公开号：US09145392B2

  公开（公告）日：2015-09-29

  The invention provides novel imidazole amine compounds according to Formula (I) and Formula (II) their manufacture and use for the treatment of hyperproliferative diseases, such as cancer.

  本发明提供了根据式(I)和式(II)的新型咪唑胺化合物，以及它们的制备方法和用于治疗增殖过度性疾病（如癌症）的用途。
• Novel Imidazole Amines as Modulators of Kinase Activity
  申请人：Merck Patent GmbH

  公开号：US20160000785A1

  公开（公告）日：2016-01-07

  The invention provides novel imidazole amine compounds according to Formula (I) and Formula (II) their manufacture and use for the treatment of hyperproliferative diseases, such as cancer.

  本发明提供了根据公式（I）和公式（II）的新型咪唑胺化合物，以及它们的制备和用于治疗高增殖性疾病，如癌症的用途。
• Rapid Development and Scale-Up of a 1<i>H</i>-4-Substituted Imidazole Intermediate Enabled by Chemistry in Continuous Plug Flow Reactors
  作者：Scott A. May、Martin D. Johnson、Timothy M. Braden、Joel R. Calvin、Brian D. Haeberle、Amy R. Jines、Richard D. Miller、Edward F. Plocharczyk、Gregory A. Rener、Rachel N. Richey、Christopher R. Schmid、Radhe K. Vaid、Hannah Yu

  DOI：10.1021/op200351g

  日期：2012.5.18

  The development of reactions in a continuous fashion in plug flow tube reactors (PFR) offers unique advantages to the drug development and scale-up process and can also enable chemistry that would be difficult to perform via batch processing. Herein, we report the development of two different continuous flow approaches to a key 1H-4-substituted imidazole intermediate (5). In a first generation approach, rapid optimization and scale-up of a challenging cyclization reaction was demonstrated in a PFR under GMP conditions to afford 29 kg of protected product 2. This material was further processed in batch equipment to deliver di-HCl salt 4. This first generation approach highlights the rapid development of chemistry in research-scale PFRs and speed to material delivery through linear scale up to a pilot-scale PFR under GMP conditions. In a second generation effort, a more efficient synthetic route was developed, and PFRs with automated sampling, dilution, and analytical analysis allowed for rapid and data-rich reaction optimization of both a key cyclization reaction and thermal removal of a Boc protecting group. This work culminated in 1 kg demonstration runs in a 0.22 L PFR for both continuous steps and shows the potential of commercialization from a lab hood footprint (1-2 MT/year).