potassium 1-cyano-1-(6-methoxy-2-methylpyridin-3-yl)prop-1-en-2-olate | 1266353-39-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: potassium 1-cyano-1-(6-methoxy-2-methylpyridin-3-yl)prop-1-en-2-olate
• CAS: 1266353-39-2
• 化学式: C₁₁H₁₁N₂O₂*K
• 分子量: 242.319
• InChiKey: YKXCFZFBBBXMOO-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.98
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  68.97
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  potassium 1-cyano-1-(6-methoxy-2-methylpyridin-3-yl)prop-1-en-2-olate 在 N-甲基吗啉 、 N,N-二异丙基乙胺 、 三氟乙酸 、 三氯氧磷 作用下， 以 水 、 异丙醇 、 乙腈 为溶剂， 反应 17.0h， 生成 Pexacerfont; 8-(6-甲氧基-2-甲基-3-吡啶基)-2,7-二甲基-N-[(1R)-1-甲基丙基]吡唑并[1,5-a]-1,3,5-三嗪-4-胺
  参考文献：
  名称：

  The Development of a Robust Process for a CRF₁ Receptor Antagonist

  摘要：

  A scalable and robust process was developed for the preparation of pexacerfont (2), a pyrazolotriazine corticotropin-releasing factor receptor 1 antagonist (CRF1). The formation of the core hydroxypyrazolotriazine moiety was achieved through two consecutive cyclizations of a semicarbazide, employing reaction conditions that are significantly milder than those reported in the literature. Further conversion to the key chloropyrazolotriazine intermediate was accomplished through a novel catalytic process using phosphorous oxychloride as the chlorinating agent. The active pharmaceutical ingredient 2 was obtained in > 99.5% purity with a 68% overall yield for the six synthetic steps.

  DOI：

  10.1021/op100270u
• 作为产物：
  描述：

  2-(6-甲氧基-2-甲基吡啶-3-基)乙腈 、 乙酸乙酯 在 potassium tert-butylate 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 potassium 1-cyano-1-(6-methoxy-2-methylpyridin-3-yl)prop-1-en-2-olate
  参考文献：
  名称：

  The Development of a Robust Process for a CRF₁ Receptor Antagonist

  摘要：

  A scalable and robust process was developed for the preparation of pexacerfont (2), a pyrazolotriazine corticotropin-releasing factor receptor 1 antagonist (CRF1). The formation of the core hydroxypyrazolotriazine moiety was achieved through two consecutive cyclizations of a semicarbazide, employing reaction conditions that are significantly milder than those reported in the literature. Further conversion to the key chloropyrazolotriazine intermediate was accomplished through a novel catalytic process using phosphorous oxychloride as the chlorinating agent. The active pharmaceutical ingredient 2 was obtained in > 99.5% purity with a 68% overall yield for the six synthetic steps.

  DOI：

  10.1021/op100270u