1-[(4-methylphenyl)sulfonyl]-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-4-carbonitrile | 68595-19-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[(4-methylphenyl)sulfonyl]-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-4-carbonitrile
• 英文别名: 5-oxo-1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-4-carbonitrile；4-Cyan-1,2,3,4-tetrahydro-1-tosyl-1-benzazepin-5-on；5-Oxo-1-tosyl-2,3,4,5-tetrahydro-1H-benzo[b]azepine-4-carbonitrile；1-(4-methylphenyl)sulfonyl-5-oxo-3,4-dihydro-2H-1-benzazepine-4-carbonitrile
• CAS: 68595-19-7
• 化学式: C₁₈H₁₆N₂O₃S
• 分子量: 340.403
• InChiKey: ROFIZBFATVJKQR-UHFFFAOYSA-N

物化性质

• 熔点：
  153-154 °C
• 沸点：
  564.5±60.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  86.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[(4-methylphenyl)sulfonyl]-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-4-carbonitrile 在 盐酸 、 palladium on activated charcoal 、 氢气 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 12.0h， 生成 1-（4-氨基苯甲酰基）-2,3,4,5-四氢苯并[b]氮杂卓-5-酮
  参考文献：
  名称：

  Practical Synthesis of N-{4-[(2-Methyl-4,5-dihydroimidazo[4,5-d][1]benzazepin- 6(1H)-yl)carbonyl]phenyl}biphenyl-2-carboxamide Monohydrochloride:  an Arginine Vasopressin Antagonist

  摘要：

  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.

  DOI：

  10.1021/op034079e
• 作为产物：
  描述：

  2-(4-甲基苯磺酰胺基)苯甲酸甲酯 在 potassium tert-butylate 、 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 、 丁酮 为溶剂， 反应 14.0h， 生成 1-[(4-methylphenyl)sulfonyl]-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-4-carbonitrile
  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

• 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.
• 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.