3-(2-chloro-4-methoxyphenyl)-4-cyano-5-morpholin-4-yl-thiophene-2-carboxylic acid amide | 1276553-10-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3-(2-chloro-4-methoxyphenyl)-4-cyano-5-morpholin-4-yl-thiophene-2-carboxylic acid amide
• CAS: 1276553-10-6
• 化学式: C₁₇H₁₆ClN₃O₃S
• 分子量: 377.851
• InChiKey: TUBCPUCJQSRDDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  88.58
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  dimethoxyformamide 、 3-(2-chloro-4-methoxyphenyl)-4-cyano-5-morpholin-4-yl-thiophene-2-carboxylic acid amide 反应 1.5h， 以95%的产率得到3-(2-chloro-4-methoxyphenyl)-4-cyano-5-morpholin-4-yl-thiophene-2-carboxylic acid [2-methylprop-(E)-ylidene] amide
  参考文献：
  名称：

  Development of Scalable Syntheses of Selective PI3K inhibitors

  摘要：

  On the basis of a more practical and scalable route to an iodothiophene, an efficient and reliable synthesis has been developed for three selective PI3K inhibitors. From this advanced intermediate, the three title compounds were each prepared in five additional steps. Key learnings also include: high throughput experimentation (HTE) screening toward a more robust Suzuki coupling, a more efficient triazole synthesis, and an acid/base cleanup developed to purify the final compounds. The final enabled synthesis required no column chromatography.

  DOI：

  10.1021/op100286g
• 作为产物：
  描述：

  3-氨基-4-氰基-5-(甲基硫代)-噻吩-2-羧酸乙酯 在 N-甲基吗啉 、 二(三叔丁基膦)钯 、 2-氯-4,6-二甲氧基-1,3,5-三嗪 、 二碘甲烷 、 oxone 、 水 、 cesium fluoride 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 25.0h， 生成 3-(2-chloro-4-methoxyphenyl)-4-cyano-5-morpholin-4-yl-thiophene-2-carboxylic acid amide
  参考文献：
  名称：

  Development of Scalable Syntheses of Selective PI3K inhibitors

  摘要：

  On the basis of a more practical and scalable route to an iodothiophene, an efficient and reliable synthesis has been developed for three selective PI3K inhibitors. From this advanced intermediate, the three title compounds were each prepared in five additional steps. Key learnings also include: high throughput experimentation (HTE) screening toward a more robust Suzuki coupling, a more efficient triazole synthesis, and an acid/base cleanup developed to purify the final compounds. The final enabled synthesis required no column chromatography.

  DOI：

  10.1021/op100286g