3-((1-methyl-1H-pyrazol-4-yl)methyl)-7-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine | 1407150-93-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 3-((1-methyl-1H-pyrazol-4-yl)methyl)-7-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine
• CAS: 1407150-93-9
• 化学式: C₁₅H₁₈N₄O₂
• 分子量: 286.334
• InChiKey: UXINUKFVTIDYHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  64.2
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-((1-methyl-1H-pyrazol-4-yl)methyl)-7-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine 在 palladium 10% on activated carbon 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 乙醇 为溶剂， 20.0~45.0 ℃ 、344.75 kPa 条件下， 反应 6.75h， 生成 [3-[(1-Methylpyrazol-4-yl)methyl]-1,2,4,5-tetrahydro-3-benzazepin-7-yl]thiourea
  参考文献：
  名称：

  Efficient and scalable synthesis of thiazole fused benzazepine as a D2 partial agonist

  摘要：

  The development of an efficient and scalable synthetic route to prepare the selective D2 partial agonist (1) is described here. Regioselective nitration of tetrahydrobenzazepine 2, followed by reductive amination, hydrogenation, and oxidative cyclization afforded 1 in good yield, without the need of column chromatography. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.035
• 作为产物：
  描述：

  1-(7-nitro-1,2,4,5-tetrahydro-3H-benzo[d]azepin-3-yl)ethan-1-one 在 盐酸 、 水 、 sodium acetate 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 生成 3-((1-methyl-1H-pyrazol-4-yl)methyl)-7-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine
  参考文献：
  名称：

  Synthesis and SAR of aminothiazole fused benzazepines as selective dopamine D2 partial agonists

  摘要：

  Dopamine (D-2) partial agonists (D2PAs) have been regarded as a potential treatment for schizophrenia patients with expected better side effect profiles than currently marketed antipsychotics. Herein we report the synthesis and SAR of a series of aminothiazole fused benzazepines as selective D-2 partial agonists. These compounds have good selectivity, CNS drug-like properties and tunable D-2 partial agonism. One of the key compounds, 8h, has good in vitro/in vivo ADME characteristics, and is active in a rat amphetamine-induced locomotor activity model. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.023