(2S)-3-(5-fluoro-1H-indol-3-yl)-2-methyl-N-{[(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl}propanamide | 1103518-36-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (2S)-3-(5-fluoro-1H-indol-3-yl)-2-methyl-N-{[(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl}propanamide
• CAS: 1103518-36-0
• 化学式: C₂₅H₂₄FN₃O₃
• 分子量: 433.482
• InChiKey: PFSVJTPLRHDZEP-KSSFIOAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  76.24
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S)-3-(5-fluoro-1H-indol-3-yl)-2-methyl-N-{[(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl}propanamide 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 以62%的产率得到WAY-262398
  参考文献：
  名称：

  First Scale-Up Synthesis of WAY-262398, a Novel, Dual-Acting SSRI/5HT1a Antagonist

  摘要：

  An alternative synthesis of WAY-262398, 1, a novel, dual-acting SSRI/5-HT(1A) antagonist, has been developed. The target compound was initially synthesized as a part of diastereomeric mixture which was separated by chiral preparative HPLC. The new route was designed around intermediates suitable for chiral resolution and/or chiral reduction of a suitable intermediate. Both processes had to be employed to achieve the target optical purity.

  DOI：

  10.1021/op8002085
• 作为产物：
  描述：

  [(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methylamine 、 (2S)-3-(5-fluoro-1H-indol-3-yl)-2-methylpropanoic acid 在 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以93%的产率得到(2S)-3-(5-fluoro-1H-indol-3-yl)-2-methyl-N-{[(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl}propanamide
  参考文献：
  名称：

  First Scale-Up Synthesis of WAY-262398, a Novel, Dual-Acting SSRI/5HT1a Antagonist

  摘要：

  An alternative synthesis of WAY-262398, 1, a novel, dual-acting SSRI/5-HT(1A) antagonist, has been developed. The target compound was initially synthesized as a part of diastereomeric mixture which was separated by chiral preparative HPLC. The new route was designed around intermediates suitable for chiral resolution and/or chiral reduction of a suitable intermediate. Both processes had to be employed to achieve the target optical purity.

  DOI：

  10.1021/op8002085