2-{5-[4-fluoro-3-(trifluoromethyl)phenyl]-2-(piperidin-4-yl)-1H-imidazol-1-yl}-N,N-dimethylethanamine | 1399035-88-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-{5-[4-fluoro-3-(trifluoromethyl)phenyl]-2-(piperidin-4-yl)-1H-imidazol-1-yl}-N,N-dimethylethanamine
• 英文别名: 2-[5-[4-fluoro-3-(trifluoromethyl)phenyl]-2-piperidin-4-ylimidazol-1-yl]-N,N-dimethylethanamine
• CAS: 1399035-88-1
• 化学式: C₁₉H₂₄F₄N₄
• 分子量: 384.42
• InChiKey: ADGACWKWUABCKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-{2-[4-fluoro-3-(trifluoromethyl)phenyl]-2-oxoethyl}isonicotinamide hydrochloride 在 盐酸 、 platinum(IV) oxide 、 氢气 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 溶剂黄146 为溶剂， 63.0~140.0 ℃ 、965.29 kPa 条件下， 反应 62.0h， 生成 2-{5-[4-fluoro-3-(trifluoromethyl)phenyl]-2-(piperidin-4-yl)-1H-imidazol-1-yl}-N,N-dimethylethanamine
  参考文献：
  名称：

  A Practical Synthesis of 2-{4-[4-Fluoro-3-(trifluoromethyl)phenyl]-2-(piperidin-4-yl)-1H-imidazol-1-yl}-N,N-dimethylethanamine

  摘要：

  A practical synthesis of the title compound was accomplished by hydrogenation of 2-{4-[4-fluoro-3-(trifluoromethyl)phenyl]-2-(pyridin-4-yl)-1H-imidazol-1-yl}-N,N-dimethylethanamine. The latter was obtained by N-alkylation of 4-{4-[4-fluoro-3-(trifluoromethyl)phenyl]-1H-imidazol-2-yl}pyridine. Treatment of N-{2-[4-fluoro-3-(trifluoromethyl)phenyl]-2-oxoethyl}isonicotinamide hydrochloride with ammonium acetate in acetic acid provided 4-{4-[4-fluoro-3-(trifluoromethyl)phenyl]-1H-imidazol-2-yl}pyridine. Coupling of 2-amino-1-[4-fluoro-3-(trifluoromethyl)phenyl]ethanone 4-methylbenzene sulfonate with pyridine 4-carboxylic acid using either T3P or EDCI-HOBt provided N-{2-[4-fluoro-3-(trifluoromethyl)phenyl]-2-oxoethyl}isonicotinamide hydrochloride.

  DOI：

  10.1055/s-0031-1290371

文献信息

• A Practical Synthesis of 2-{4-[4-Fluoro-3-(trifluoromethyl)phenyl]-2-(piperidin-4-yl)-1H-imidazol-1-yl}-N,N-dimethylethanamine
  作者：Radhe Vaid、Jeremy Spitler、Sathish Boini、Kenneth Henry、Xu Jiansheng、Baitao Gao、Xiaoquan Lu

  DOI：10.1055/s-0031-1290371

  日期：2012.7

  A practical synthesis of the title compound was accomplished by hydrogenation of 2-4-[4-fluoro-3-(trifluoromethyl)phenyl]-2-(pyridin-4-yl)-1H-imidazol-1-yl}-N,N-dimethylethanamine. The latter was obtained by N-alkylation of 4-4-[4-fluoro-3-(trifluoromethyl)phenyl]-1H-imidazol-2-yl}pyridine. Treatment of N-2-[4-fluoro-3-(trifluoromethyl)phenyl]-2-oxoethyl}isonicotinamide hydrochloride with ammonium acetate in acetic acid provided 4-4-[4-fluoro-3-(trifluoromethyl)phenyl]-1H-imidazol-2-yl}pyridine. Coupling of 2-amino-1-[4-fluoro-3-(trifluoromethyl)phenyl]ethanone 4-methylbenzene sulfonate with pyridine 4-carboxylic acid using either T3P or EDCI-HOBt provided N-2-[4-fluoro-3-(trifluoromethyl)phenyl]-2-oxoethyl}isonicotinamide hydrochloride.