8-hydroxy-2,3-dimethyl-7-(3-oxo-3-phenylpropyl)imidazo[1,2-a]pyridine-6-carboxylic acid cyclopropylamide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-hydroxy-2,3-dimethyl-7-(3-oxo-3-phenylpropyl)imidazo[1,2-a]pyridine-6-carboxylic acid cyclopropylamide
• 英文别名: 8-hydroxy-2,3-dimethyl-7-(3-oxo-3-phenyl-propyl)-imidazo[1,2-a]pyridine-6-carboxylic acid cyclopropylamide；N-cyclopropyl-8-hydroxy-2,3-dimethyl-7-(3-oxo-3-phenylpropyl)imidazo[1,2-a]pyridine-6-carboxamide
• 化学式: C₂₂H₂₃N₃O₃
• 分子量: 377.443
• InChiKey: JMDNECKCIQCREB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  83.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-hydroxy-2,3-dimethyl-7-(3-oxo-3-phenylpropyl)imidazo[1,2-a]pyridine-6-carboxylic acid cyclopropylamide 在 RuCl₂[(S)-Xyl-P-Phos][(S)-DAIPEN] potassium tert-butylate 、 氢气 作用下， 以 水 、 异丙醇 、 叔丁醇 为溶剂， 55.0~85.0 ℃ 、1.0 MPa 条件下， 反应 72.0h， 以25%的产率得到(3R)-8-hydroxy-7-(3-hydroxy-3-phenylpropyl)-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylic acid cyclopropylamide
  参考文献：
  名称：

  Preparation of tricyclic imidazopyridines by asymmetric ketone hydrogenation in the presence of RuCl2[(S)-Xyl-P-Phos][(S)-DAIPEN]

  摘要：

  The novel complex RuCl2[(S)-Xyl-P-Phos][(S)-DAIPEN] was identified as a highly active catalyst for the asymmetric reduction of a variety of prochiral ketones possessing an imidazo[1,2-a]pyridine scaffold. The corresponding alcohols were obtained in excellent enantiomeric purities (>96% ee) and served as valuable intermediates for the synthesis of pharmacologically active 7H-8,9-dihydropyrano[2,3-c]imidazo[ 1,2-alpyridines. The complexity of these multi-functional substrates required the development of specific reaction conditions. Whereas the reduction with RuCl2[PP][NN] catalysts (Noyori catalysts) has never been reported to occur under aqueous conditions, in the present case, the use of aqueous isopropanol or tert-butanol was not only tolerated, but also turned out to be beneficial, especially when the reduction was conducted at high substrate to catalyst (S/C) ratios. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.05.013
• 作为产物：
  描述：

  9-methoxy-2,3-dimethyl-9-phenyl-7H-8,9-dihydropyrano[2,3-c]imidazo[1,2-a]pyridine-6-carboxylic acid cyclopropylamide 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以78%的产率得到8-hydroxy-2,3-dimethyl-7-(3-oxo-3-phenylpropyl)imidazo[1,2-a]pyridine-6-carboxylic acid cyclopropylamide
  参考文献：
  名称：

  Preparation of tricyclic imidazopyridines by asymmetric ketone hydrogenation in the presence of RuCl2[(S)-Xyl-P-Phos][(S)-DAIPEN]

  摘要：

  The novel complex RuCl2[(S)-Xyl-P-Phos][(S)-DAIPEN] was identified as a highly active catalyst for the asymmetric reduction of a variety of prochiral ketones possessing an imidazo[1,2-a]pyridine scaffold. The corresponding alcohols were obtained in excellent enantiomeric purities (>96% ee) and served as valuable intermediates for the synthesis of pharmacologically active 7H-8,9-dihydropyrano[2,3-c]imidazo[ 1,2-alpyridines. The complexity of these multi-functional substrates required the development of specific reaction conditions. Whereas the reduction with RuCl2[PP][NN] catalysts (Noyori catalysts) has never been reported to occur under aqueous conditions, in the present case, the use of aqueous isopropanol or tert-butanol was not only tolerated, but also turned out to be beneficial, especially when the reduction was conducted at high substrate to catalyst (S/C) ratios. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.05.013

文献信息

• WO2007/141253
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] PROCESS FOR THE PRODUCTION OF INTERMEDIATES FOR THE PREPARATION OF TRICYCLIC IMIDAZOPYRIDINES<br/>[FR] PROCÉDÉ DE PRODUCTION D'INTERMÉDIAIRES POUR LA PRÉPARATION D'IMIDAZOPYRIDINES TRICYCLIQUES
  申请人：NYCOMED GMBH

  公开号：WO2007141253A1

  公开（公告）日：2007-12-13

  [EN] The invention relates to a process for the synthesis of compounds of the formula (1-a) and compounds of the formula (1-b). The compounds of the formula 1-a and the compounds of the formula 1-b, in which the substituents R1, R2, R3, and Arom have the meanings indicated in the description, are valuable intermediates for the preparation of pharmaceutically active compounds.
  [FR] La présente invention concerne un procédé de synthèse de composés répondant à la formule (1-a) et de composés répondant à la formule (1-b). Les composés de la formule 1-a et les composés de la formule 1-b, les substituants R1, R2, R3 et Arom étant tels que définis dans la description, sont des intermédiaires utiles pour la préparation de composés pharmaceutiquement actifs.
• Preparation of tricyclic imidazopyridines by asymmetric ketone hydrogenation in the presence of RuCl2[(S)-Xyl-P-Phos][(S)-DAIPEN]
  作者：Andreas Marc Palmer、Antonio Zanotti-Gerosa、Hans Nedden

  DOI：10.1016/j.tetasy.2008.05.013

  日期：2008.6

  The novel complex RuCl2[(S)-Xyl-P-Phos][(S)-DAIPEN] was identified as a highly active catalyst for the asymmetric reduction of a variety of prochiral ketones possessing an imidazo[1,2-a]pyridine scaffold. The corresponding alcohols were obtained in excellent enantiomeric purities (>96% ee) and served as valuable intermediates for the synthesis of pharmacologically active 7H-8,9-dihydropyrano[2,3-c]imidazo[ 1,2-alpyridines. The complexity of these multi-functional substrates required the development of specific reaction conditions. Whereas the reduction with RuCl2[PP][NN] catalysts (Noyori catalysts) has never been reported to occur under aqueous conditions, in the present case, the use of aqueous isopropanol or tert-butanol was not only tolerated, but also turned out to be beneficial, especially when the reduction was conducted at high substrate to catalyst (S/C) ratios. (C) 2008 Elsevier Ltd. All rights reserved.