C-(4-{N'-[5-Chloro-pent-(E)-ylidene]-hydrazino}-phenyl)-N-methyl-methanesulfonamide | 201798-91-6

• 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: C-(4-{N'-[5-Chloro-pent-(E)-ylidene]-hydrazino}-phenyl)-N-methyl-methanesulfonamide
• 英文别名: 1-[4-[2-(5-chloropentylidene)hydrazinyl]phenyl]-N-methylmethanesulfonamide
• CAS: 201798-91-6
• 化学式: C₁₃H₂₀ClN₃O₂S
• 分子量: 317.84
• InChiKey: HFONHAODQGNRLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.54
• 重原子数：
  20.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  70.56
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  C-(4-{N'-[5-Chloro-pent-(E)-ylidene]-hydrazino}-phenyl)-N-methyl-methanesulfonamide 在 磷酸 作用下， 以 乙酸丁酯 为溶剂， 生成 N-methyl-3-(3'-chloropropyl)-1H-indolyl-5-methanesulfonamide 、 N-Methyl-C-{3-[3-(tetrahydro-pyran-2-yloxy)-propyl]-1H-indol-5-yl}-methanesulfonamide 、 C-[3-(3-Hydroxy-propyl)-1-(tetrahydro-pyran-2-yl)-1H-indol-5-yl]-N-methyl-methanesulfonamide 、 C-[3,3'-Bis-(3-hydroxy-propyl)-1H,1'H-[2,5']biindolyl-5-yl]-N-methyl-methanesulfonamide
  参考文献：
  名称：

  An Efficient Fischer Indole Synthesis of Avitriptan, a Potent 5-HT_1D Receptor Agonist

  摘要：

  An efficient synthesis of the antimigraine drug candidate avitriptan (1, BMS 180048) is reported. The key step is a two-phase Fischer indolization reaction between hydrazine 6 and 5-chlorovaleraldehyde, 20, to give the chloropropylindole 35, which is susceptible to acid-catalyzed degradation under the reaction conditions required for its formation. Sequential coupling of 35 with piperazine, 26, and 4-chloro-5-methoxypyrimidine, 24, gives the title compound in 40-45% overall yield. Significant improvements in the syntheses of the known starting materials, hydrazine 6, 5-chlorovaleraldehyde, 20, and 4-chloro-5-methoxypyrimidine, 24, were also achieved.

  DOI：

  10.1021/jo971368q
• 作为产物：
  描述：

  四氢吡喃 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 三乙胺 、 zinc(II) chloride 作用下， 以 乙酸丁酯 为溶剂， 反应 1.5h， 生成 C-(4-{N'-[5-Chloro-pent-(E)-ylidene]-hydrazino}-phenyl)-N-methyl-methanesulfonamide
  参考文献：
  名称：

  An Efficient Fischer Indole Synthesis of Avitriptan, a Potent 5-HT_1D Receptor Agonist

  摘要：

  An efficient synthesis of the antimigraine drug candidate avitriptan (1, BMS 180048) is reported. The key step is a two-phase Fischer indolization reaction between hydrazine 6 and 5-chlorovaleraldehyde, 20, to give the chloropropylindole 35, which is susceptible to acid-catalyzed degradation under the reaction conditions required for its formation. Sequential coupling of 35 with piperazine, 26, and 4-chloro-5-methoxypyrimidine, 24, gives the title compound in 40-45% overall yield. Significant improvements in the syntheses of the known starting materials, hydrazine 6, 5-chlorovaleraldehyde, 20, and 4-chloro-5-methoxypyrimidine, 24, were also achieved.

  DOI：

  10.1021/jo971368q