N-(3-(2-chlorophenyl)-4-(4-chlorophenyl)-1H-pyrazol-5-yl)acetamidine | 1153577-09-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-(3-(2-chlorophenyl)-4-(4-chlorophenyl)-1H-pyrazol-5-yl)acetamidine
• 英文别名: N'-[5-(2-chlorophenyl)-4-(4-chlorophenyl)-1H-pyrazol-3-yl]ethanimidamide
• CAS: 1153577-09-3
• 化学式: C₁₇H₁₄Cl₂N₄
• 分子量: 345.231
• InChiKey: AQMYYTLOMZUEFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  67.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-(2-chlorophenyl)-4-(4-chlorophenyl)-1H-pyrazol-5-yl)acetamidine 、 N,N'-羰基二咪唑 在 盐酸 作用下， 以 二甲基亚砜 、 水 为溶剂， 反应 3.0h， 以6.4 g的产率得到7-(2-chlorophenyl)-8-(4-chlorophenyl)-2-methylpyrazolo[1,5-a][1,3,5]triazin-4(3H)-one
  参考文献：
  名称：

  Development of two synthetic routes to CE-178,253, a CB1 antagonist for the treatment of obesity

  摘要：

  CE-178,253 benzenesulfonate (1) is a CB1 antagonist discovered by Pfizer medicinal chemists. Two syntheses Of this compound are described. The first, based on the discovery synthesis, involves assembly of an aryl-substituted pyrazolotriazine core onto which the second aryl moiety is installed by a Suzuki Coupling: this route has been scaled to provide up to 6 kg of API. A second. more convergent route is also described, which installs the pyrazolotriazine containing both aryl substituents by condensation of a bromoketone with a substituted thiosemicarbazide. This route has been demonstrated on laboratory scale and is viewed as the preferred bond-forming sequence. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.10.067
• 作为产物：
  描述：

  N-(3-(2-chlorophenyl)-4-(4-chlorophenyl)-1H-pyrazol-5-yl)acetamidine hydrobromide 在 sodium hydroxide 、 水 作用下， 以 2-甲基四氢呋喃 为溶剂， 生成 N-(3-(2-chlorophenyl)-4-(4-chlorophenyl)-1H-pyrazol-5-yl)acetamidine
  参考文献：
  名称：

  Development of two synthetic routes to CE-178,253, a CB1 antagonist for the treatment of obesity

  摘要：

  CE-178,253 benzenesulfonate (1) is a CB1 antagonist discovered by Pfizer medicinal chemists. Two syntheses Of this compound are described. The first, based on the discovery synthesis, involves assembly of an aryl-substituted pyrazolotriazine core onto which the second aryl moiety is installed by a Suzuki Coupling: this route has been scaled to provide up to 6 kg of API. A second. more convergent route is also described, which installs the pyrazolotriazine containing both aryl substituents by condensation of a bromoketone with a substituted thiosemicarbazide. This route has been demonstrated on laboratory scale and is viewed as the preferred bond-forming sequence. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.10.067