(3S,5S)-5-[3,3-dimethyl-1-(o-tolyl)-6-oxo-2H-pyridin-4-yl]-N-[(1R)-1-(5-fluoro-2-pyridyl)-3-methylbutyl]piperidine-3-carboxamide fumarate | 1620523-79-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S,5S)-5-[3,3-dimethyl-1-(o-tolyl)-6-oxo-2H-pyridin-4-yl]-N-[(1R)-1-(5-fluoro-2-pyridyl)-3-methylbutyl]piperidine-3-carboxamide fumarate
• 英文别名: (E)-but-2-enedioic acid;(3S,5S)-5-[3,3-dimethyl-1-(2-methylphenyl)-6-oxo-2H-pyridin-4-yl]-N-[(1R)-1-(5-fluoropyridin-2-yl)-3-methylbutyl]piperidine-3-carboxamide
• CAS: 1620523-79-6
• 化学式: C₄H₄O₄*C₃₀H₃₉FN₄O₂
• 分子量: 622.737
• InChiKey: BDARKRJWOGUFHF-XUHZOOQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  45
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  149
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1-(tert-butoxycarbonyl)-5-(methoxycarbonyl)piperidine-3-carboxylic acid 在 硼烷四氢呋喃络合物 、 草酰氯 、 18-冠醚-6 、 lithium hydroxide monohydrate 、 氯化铵 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 臭氧 、 溶剂黄146 、 N,N-二异丙基乙胺 、 三氟乙酸 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 34.83h， 生成 (3S,5S)-5-[3,3-dimethyl-1-(o-tolyl)-6-oxo-2H-pyridin-4-yl]-N-[(1R)-1-(5-fluoro-2-pyridyl)-3-methylbutyl]piperidine-3-carboxamide fumarate
  参考文献：
  名称：

  An Efficient Synthesis of (3S,5S)-5-[3,3-Dimethyl-1-(o-tolyl)-6-oxo-2H-pyridin-4-yl]piperidine-3-carboxamide as Potent Renin Inhibitor

  摘要：

  We report synthesis and biological evaluation of (3S,5S)-5-[3,3-dimethyl-1-(o-tolyl)-6-oxo-2H-pyridin-4-yl]piperidine-3-carboxamide as renin inhibitor. This effective synthetic route involves a zinc mediated Barbier reaction and an intramolecular Horner-Wadsworth-Emmons reaction of sterically hindered ketone as key reactions. The prepared compound 4 exhibited both potent renin inhibitory activity and significant in vivo efficacy in furosemide pretreated cynomolgus monkeys.

  DOI：

  10.3987/com-14-12988

文献信息

• An Efficient Synthesis of (3S,5S)-5-[3,3-Dimethyl-1-(o-tolyl)-6-oxo-2H-pyridin-4-yl]piperidine-3-carboxamide as Potent Renin Inhibitor
  作者：Yutaka Mori、Mitsuhiro Iwamoto、Kazuki Mori、Masao Yoshida、Takeshi Honda、Takahiro Nagayama、Takahide Nishi

  DOI：10.3987/com-14-12988

  日期：——

  We report synthesis and biological evaluation of (3S,5S)-5-[3,3-dimethyl-1-(o-tolyl)-6-oxo-2H-pyridin-4-yl]piperidine-3-carboxamide as renin inhibitor. This effective synthetic route involves a zinc mediated Barbier reaction and an intramolecular Horner-Wadsworth-Emmons reaction of sterically hindered ketone as key reactions. The prepared compound 4 exhibited both potent renin inhibitory activity and significant in vivo efficacy in furosemide pretreated cynomolgus monkeys.