(3R,4R)-4-(benzylamino)-1-[[4-(3-methoxyanilino)pyrrolo[2,1-f][1,2,4]triazin-5-yl]methyl]piperidin-3-ol | 1426125-47-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (3R,4R)-4-(benzylamino)-1-[[4-(3-methoxyanilino)pyrrolo[2,1-f][1,2,4]triazin-5-yl]methyl]piperidin-3-ol
• CAS: 1426125-47-4
• 化学式: C₂₆H₃₀N₆O₂
• 分子量: 458.563
• InChiKey: RSTKTHNNNQLEPS-DNQXCXABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3R,4R)-4-(benzylamino)-1-[[4-(3-methoxyanilino)pyrrolo[2,1-f][1,2,4]triazin-5-yl]methyl]piperidin-3-ol 在 10 wt% Pd(OH)2 on carbon 、 氢气 、 sodium carbonate 作用下， 以 异丁醇 、 水 、 甲苯 为溶剂， 45.0 ℃ 、308.18 kPa 条件下， 以89%的产率得到(3R,4R)-4-氨基-1-[[4-[(3-甲氧基苯基)氨基]吡咯并[2,1-f][1,2,4]三嗪-5-基]甲基]哌啶-3-醇
  参考文献：
  名称：

  Evolution of the Process for the Preparation of a Selective ErbB VEGF Receptor Inhibitor

  摘要：

  An efficient synthetic route to the potent and selective ErbB VEGF receptor inhibitor, BMS-690514 (1) is described. Strategic modifications in both approach and procedure addressed several issues, which led to a safe, efficient, and economical process for the preparation of multi-kilogram quantities of 1. The convergent route involves alkylation of a suitably protected (3R,4R)-4-aminopiperidin-3-ol with the triethyl(alkyl) ammonium salt of a functionalized pyrrolotriazine 3a followed by deprotection to provide 1 as the crystalline free base.

  DOI：

  10.1055/s-0032-1317540
• 作为产物：
  描述：

  (4-(3-methoxyphenylamino)pyrrolo[1,2-f][1,2,4]-triazin-5-yl)methanol 在 甲烷磺酸 作用下， 以 N-甲基吡咯烷酮 、 水 、 乙腈 为溶剂， 反应 3.5h， 生成 (3R,4R)-4-(benzylamino)-1-[[4-(3-methoxyanilino)pyrrolo[2,1-f][1,2,4]triazin-5-yl]methyl]piperidin-3-ol
  参考文献：
  名称：

  Evolution of the Process for the Preparation of a Selective ErbB VEGF Receptor Inhibitor

  摘要：

  An efficient synthetic route to the potent and selective ErbB VEGF receptor inhibitor, BMS-690514 (1) is described. Strategic modifications in both approach and procedure addressed several issues, which led to a safe, efficient, and economical process for the preparation of multi-kilogram quantities of 1. The convergent route involves alkylation of a suitably protected (3R,4R)-4-aminopiperidin-3-ol with the triethyl(alkyl) ammonium salt of a functionalized pyrrolotriazine 3a followed by deprotection to provide 1 as the crystalline free base.

  DOI：

  10.1055/s-0032-1317540