2,4-二溴-6-(2-氯苯基)-5-甲基吡啶-3-胺 | 906463-07-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2,4-二溴-6-(2-氯苯基)-5-甲基吡啶-3-胺
• 英文名称: 2,4-Dibromo-6-(2-chlorophenyl)-5-methyl-3-pyridinamine
• 英文别名: 2,4-dibromo-6-(2-chlorophenyl)-5-methylpyridin-3-amine
• CAS: 906463-07-8
• 化学式: C₁₂H₉Br₂ClN₂
• 分子量: 376.478
• InChiKey: YJQCRGYCIOCWEJ-UHFFFAOYSA-N

物化性质

• 沸点：
  390.4±37.0 °C(Predicted)
• 密度：
  1.785±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  38.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4-二溴-6-(2-氯苯基)-5-甲基吡啶-3-胺 在 Adam’s catalyst 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 四(三苯基膦)钯 、 氢气 、 potassium carbonate 、 三氟乙酸 、 亚硝酸异戊酯 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0~150.0 ℃ 、137.9 kPa 条件下， 反应 2.15h， 生成 5-(2-Chloro-phenyl)-1-(2,6-dichloro-phenyl)-7-piperidin-4-yl-3,4-dihydro-1H-pyrido[4,3-d]pyrimidin-2-one
  参考文献：
  名称：

  p38 MAP kinase inhibitors. Part 3: SAR on 3,4-dihydropyrimido[4,5-d]pyrimidin-2-ones and 3,4-dihydropyrido[4,3-d]pyrimidin-2-ones

  摘要：

  p38 inhibitors based on 3,4-dihydropyrimido[4,5-d]pyrimidin-2-one and 3,4-dihydropyrido[4,3-d]pyrimidin-2-one platforms were synthesized and preliminary SAR explored. Among the pyrimido-pyrimidones the emergence of two sub-types of analogs-C7-amino-pyrimidines such as 24 and C7-amino-piperidines such as 42-characterized with good p38 inhibition and better off-target profiles in terms of ion channel activities was significant. Representative compound 54 in the pyrido-pyrimidone class was found to be equipotent with corresponding analog in the quinazolinone series. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.045
• 作为产物：
  描述：

  2-氯-3-甲基-5-硝基吡啶 在 盐酸 、 四(三苯基膦)钯 、 溴 、 镍 、 caesium carbonate 作用下， 生成 2,4-二溴-6-(2-氯苯基)-5-甲基吡啶-3-胺
  参考文献：
  名称：

  p38 Inhibitors: piperidine- and 4-aminopiperidine-substituted naphthyridinones, quinolinones, and dihydroquinazolinones

  摘要：

  We have synthesized a series of C7-piperidine- and 4-aminopiperidine-substituted naphthyridinones, quinolinones, and dihydroquinazolinones that are highly potent inhibitors of both p38 MAP kinase activity and TNF-alpha release. The 4-aminopenta-methylpiperidine naphthyridinone 5, which was designed to block metabolism at major 'hot spots', combined excellent inhibitory potency with good oral bioavailability in the rat. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00990-3

文献信息

• p38 Inhibitors: piperidine- and 4-aminopiperidine-substituted naphthyridinones, quinolinones, and dihydroquinazolinones
  作者：Julianne A Hunt、Florida Kallashi、Rowena D Ruzek、Peter J Sinclair、Ida Ita、Sherrie X McCormick、James V Pivnichny、C.E.C.A Hop、Sanjeev Kumar、Zhen Wang、Stephen J O'Keefe、Edward A O'Neill、Gene Porter、James E Thompson、Andrea Woods、Dennis M Zaller、James B Doherty

  DOI：10.1016/s0960-894x(02)00990-3

  日期：2003.2

  We have synthesized a series of C7-piperidine- and 4-aminopiperidine-substituted naphthyridinones, quinolinones, and dihydroquinazolinones that are highly potent inhibitors of both p38 MAP kinase activity and TNF-alpha release. The 4-aminopenta-methylpiperidine naphthyridinone 5, which was designed to block metabolism at major 'hot spots', combined excellent inhibitory potency with good oral bioavailability in the rat. (C) 2002 Elsevier Science Ltd. All rights reserved.
• p38 MAP kinase inhibitors. Part 3: SAR on 3,4-dihydropyrimido[4,5-d]pyrimidin-2-ones and 3,4-dihydropyrido[4,3-d]pyrimidin-2-ones
  作者：Swaminathan R. Natarajan、David D. Wisnoski、James E. Thompson、Edward A. O’Neill、Stephen J. O’Keefe

  DOI：10.1016/j.bmcl.2006.05.045

  日期：2006.8

  p38 inhibitors based on 3,4-dihydropyrimido[4,5-d]pyrimidin-2-one and 3,4-dihydropyrido[4,3-d]pyrimidin-2-one platforms were synthesized and preliminary SAR explored. Among the pyrimido-pyrimidones the emergence of two sub-types of analogs-C7-amino-pyrimidines such as 24 and C7-amino-piperidines such as 42-characterized with good p38 inhibition and better off-target profiles in terms of ion channel activities was significant. Representative compound 54 in the pyrido-pyrimidone class was found to be equipotent with corresponding analog in the quinazolinone series. (c) 2006 Elsevier Ltd. All rights reserved.