2-[(3R)-3-aminopiperidin-1-yl]-3-(2-chlorobenzyl)-8-methoxy-5-methyl-3,5-dihydro-4H-imidazo[4,5-c]quinolin-4-one hydrochloride | 1349877-77-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-[(3R)-3-aminopiperidin-1-yl]-3-(2-chlorobenzyl)-8-methoxy-5-methyl-3,5-dihydro-4H-imidazo[4,5-c]quinolin-4-one hydrochloride
• 英文别名: 2-[(3R)-3-aminopiperidin-1-yl]-3-[(2-chlorophenyl)methyl]-8-methoxy-5-methylimidazo[4,5-c]quinolin-4-one;hydrochloride
• CAS: 1349877-77-5
• 化学式: C₂₄H₂₆ClN₅O₂*ClH
• 分子量: 488.417
• InChiKey: YEHGSEDYNCYHBQ-PKLMIRHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  76.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  tert-butyl (R)-(1-(1-(2-chlorobenzyl)-4-iodo-5-((4-methoxyphenyl)(methyl)carbamoyl)-1H-imidazol-2-yl)piperidin-3-yl)carbamate 在 盐酸 、 palladium diacetate 、 三苯基膦 、 silver carbonate 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 2-[(3R)-3-aminopiperidin-1-yl]-3-(2-chlorobenzyl)-8-methoxy-5-methyl-3,5-dihydro-4H-imidazo[4,5-c]quinolin-4-one hydrochloride
  参考文献：
  名称：

  Preparation of 2-aminosubstituted 3H-imidazo[4,5-c]quinolin-4(5H)-ones by palladium-assisted internal biaryl coupling reaction

  摘要：

  Representatives of the 3H-imidazo[4,5-c]quinolin-4(5H)-ones have shown interesting biological activity. We have found 2-aminosubstituted 3H-imidazo[4,5-c]quinolin-4(5H)-one as a potent dipeptidyl peptidase 4 inhibitor. However effective synthesis of this nucleus with various substituents at the 6-9-positions has not been reported. We report herein the development of a novel and efficient synthesis of 2-aminosubstituted 3H-imidazo[4,5-c]quinolin-4(5H)-ones by palladium-assisted internal biaryl coupling reaction. Our optimization of the reaction conditions revealed that the most important factors for this reaction are use of silver carbonate as a base and high reaction temperature. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.015

文献信息

• Preparation of 2-aminosubstituted 3H-imidazo[4,5-c]quinolin-4(5H)-ones by palladium-assisted internal biaryl coupling reaction
  作者：Yohei Ikuma、Hiroyuki Nakahira

  DOI：10.1016/j.tet.2011.10.015

  日期：2011.12

  Representatives of the 3H-imidazo[4,5-c]quinolin-4(5H)-ones have shown interesting biological activity. We have found 2-aminosubstituted 3H-imidazo[4,5-c]quinolin-4(5H)-one as a potent dipeptidyl peptidase 4 inhibitor. However effective synthesis of this nucleus with various substituents at the 6-9-positions has not been reported. We report herein the development of a novel and efficient synthesis of 2-aminosubstituted 3H-imidazo[4,5-c]quinolin-4(5H)-ones by palladium-assisted internal biaryl coupling reaction. Our optimization of the reaction conditions revealed that the most important factors for this reaction are use of silver carbonate as a base and high reaction temperature. (C) 2011 Elsevier Ltd. All rights reserved.