(S)-3-(1-(2-amino-6-chloropyrimidin-4-yl)piperidin-3-yl)-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one | 1330191-73-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: (S)-3-(1-(2-amino-6-chloropyrimidin-4-yl)piperidin-3-yl)-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one
• CAS: 1330191-73-5
• 化学式: C₁₇H₂₀ClN₇O
• 分子量: 373.845
• InChiKey: IQIZENPDIQFGFI-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  94.86
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  苯并呋喃-2-硼酸 、 (S)-3-(1-(2-amino-6-chloropyrimidin-4-yl)piperidin-3-yl)-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 甲醇 、 苯 为溶剂， 以52%的产率得到(S)-3-(1-(2-amino-6-(benzofuran-2-yl)pyrimidin-4-yl)piperidin-3-yl)-1-ethyl-1H-imidazo[4,5-b]pyridin-2(3H)-one
  参考文献：
  名称：

  Identification of potent, noncovalent fatty acid amide hydrolase (FAAH) inhibitors

  摘要：

  Starting from a series of ureas that were determined to be mechanism-based inhibitors of FAAH, several spirocyclic ureas and lactams were designed and synthesized. These efforts identified a series of novel, noncovalent FAAH inhibitors with in vitro potency comparable to known covalent FAAH inhibitors. The mechanism of action for these compounds was determined through a combination of SAR and co-crystallography with rat FAAH. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.052
• 作为产物：
  描述：

  tert-butyl (3S)-3-(2-nitroanilino)piperidine-1-carboxylate 在 盐酸 、 palladium 10% on activated carbon 、 水 、 氢气 、 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 生成 (S)-3-(1-(2-amino-6-chloropyrimidin-4-yl)piperidin-3-yl)-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one
  参考文献：
  名称：

  Identification of potent, noncovalent fatty acid amide hydrolase (FAAH) inhibitors

  摘要：

  Starting from a series of ureas that were determined to be mechanism-based inhibitors of FAAH, several spirocyclic ureas and lactams were designed and synthesized. These efforts identified a series of novel, noncovalent FAAH inhibitors with in vitro potency comparable to known covalent FAAH inhibitors. The mechanism of action for these compounds was determined through a combination of SAR and co-crystallography with rat FAAH. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.052