{4-[(2-methyl-4,5-dihydroimidazo[4,5-d][1]benzazepin-6(1H)-yl)carbonyl]phenyl}amine | 195531-22-7

• 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: {4-[(2-methyl-4,5-dihydroimidazo[4,5-d][1]benzazepin-6(1H)-yl)carbonyl]phenyl}amine
• 英文别名: (4-aminophenyl)-(2-methyl-4,5-dihydro-3H-imidazo[4,5-d][1]benzazepin-6-yl)methanone
• CAS: 195531-22-7
• 化学式: C₁₉H₁₈N₄O
• 分子量: 318.378
• InChiKey: HBUXZDWBSFNLEW-UHFFFAOYSA-N

物化性质

• 熔点：
  >250 °C
• 沸点：
  682.3±55.0 °C(Predicted)
• 密度：
  1.315±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  75
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  {4-[(2-methyl-4,5-dihydroimidazo[4,5-d][1]benzazepin-6(1H)-yl)carbonyl]phenyl}amine 、 二氢-3-(异十二碳烯基)呋喃-2,5-二酮 在 吡啶 、 草酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 以74%的产率得到盐酸考尼伐坦
  参考文献：
  名称：

  A New Synthetic Route to YM087, an Arginine Vasopressin Antagonist

  摘要：

  A new synthesis of N-{4-[(2-methyl-4,5-dihydroimidazo[4,5-d][1]benzazepin-6(1H)-yl)carbonyl]phenyl}biphenyl-2-carboxamide monohydrochloride (1, YM087) via new imidazobenzazepine intermediates is described. This method remarkably improves the overall yield of 1 compared to the original synthesis providing a more safe, reliable and cost-efficient approach to 1.

  DOI：

  10.3987/com-04-10025
• 作为产物：
  描述：

  2-(4-甲基苯磺酰胺基)苯甲酸甲酯 在 镍 盐酸 、 硫酸 、 potassium tert-butylate 、 氢气 、 吡啶盐酸盐 、 pyridinium hydrobromide perbromide 、 potassium carbonate 、 溶剂黄146 、 potassium iodide 作用下， 以 甲醇 、 氯仿 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 丁酮 为溶剂， 反应 177.0h， 生成 {4-[(2-methyl-4,5-dihydroimidazo[4,5-d][1]benzazepin-6(1H)-yl)carbonyl]phenyl}amine
  参考文献：
  名称：

  A New Synthetic Route to YM087, an Arginine Vasopressin Antagonist

  摘要：

  A new synthesis of N-{4-[(2-methyl-4,5-dihydroimidazo[4,5-d][1]benzazepin-6(1H)-yl)carbonyl]phenyl}biphenyl-2-carboxamide monohydrochloride (1, YM087) via new imidazobenzazepine intermediates is described. This method remarkably improves the overall yield of 1 compared to the original synthesis providing a more safe, reliable and cost-efficient approach to 1.

  DOI：

  10.3987/com-04-10025

文献信息

• 1,2-Disubstituted bicyclo[2.1.1]hexanes as saturated bioisosteres of <i>ortho</i>-substituted benzene
  作者：Aleksandr Denisenko、Pavel Garbuz、Yelyzaveta Makovetska、Oleh Shablykin、Dmytro Lesyk、Galeb Al-Maali、Rodion Korzh、Iryna V. Sadkova、Pavel K. Mykhailiuk

  DOI：10.1039/d3sc05121h

  日期：——

  Bicyclo[2.1.1]hexanes have been synthesized, characterized, and biologically validated as saturated bioisosteres of the ortho-substituted benzene ring. The incorporation of the 1,2-disubstituted bicyclo[2.1.1]hexane core into the structure of fungicides boscalid (BASF), bixafen (Bayer CS), and fluxapyroxad (BASF) gave saturated patent-free analogs with high antifungal activity.

  双环[2.1.1]己烷已被合成、表征和生物学验证为邻位取代苯环的饱和生物等排体。将 1,2-二取代的双环[2.1.1]己烷核心纳入杀菌剂啶酰菌胺 (BASF)、bixafen (拜耳 CS) 和 Fluxapyroxad (BASF) 的结构中，得到具有高抗真菌活性的饱和无专利类似物。
• Practical Synthesis of <i>N</i>-{4-[(2-Methyl-4,5-dihydroimidazo[4,5-<i>d</i>][1]benzazepin- 6(1<i>H</i>)-yl)carbonyl]phenyl}biphenyl-2-carboxamide Monohydrochloride:  an Arginine Vasopressin Antagonist
  作者：Takashi Tsunoda、Atsuki Yamazaki、Hidenori Iwamoto、Shuichi Sakamoto

  DOI：10.1021/op034079e

  日期：2003.11.1

  A novel, reliable, and cost-effective synthetic route to N-4-[(2-methyl-4,5-dihydroimidazo[4,5-d][1]benzazepin-6(1H)-yl)carbonyl]-phenyl}biphenyl-2-carboxamide monohydrochloride (1, YM087), a potent Arginine vasopressin antagonist, has been developed. Using moisture-controlled potassium carbonate, imidazole formation from alpha-bromoketone furnished imidazobenzazepine, avoiding potential oxazole-ring formation. Catalytic reduction of nitro imidazobenzazepine afforded the corresponding amine in high yields. Treatment of the imidazole-containing amine directly, with a carbonyl chloride, afforded the target amide circumventing protection of the imidazole.
• Drugs. Fut. 2000, 25, 1121-1130
  作者：

  DOI：——

  日期：——
• A New Synthetic Route to YM087, an Arginine Vasopressin Antagonist
  作者：Takashi Tsunoda、Akihiro Tanaka、Toshiyasu Mase、Shuichi Sakamoto

  DOI：10.3987/com-04-10025

  日期：——

  A new synthesis of N-4-[(2-methyl-4,5-dihydroimidazo[4,5-d][1]benzazepin-6(1H)-yl)carbonyl]phenyl}biphenyl-2-carboxamide monohydrochloride (1, YM087) via new imidazobenzazepine intermediates is described. This method remarkably improves the overall yield of 1 compared to the original synthesis providing a more safe, reliable and cost-efficient approach to 1.