4-(4-氰基-2-氟苯基)-2-吗啉-5-(1H-1,2,4-三唑-5-基)噻吩-3-腈 | 1276553-09-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 4-(4-氰基-2-氟苯基)-2-吗啉-5-(1H-1,2,4-三唑-5-基)噻吩-3-腈
• 英文名称: 4-(4-cyano-2-fluorophenyl)-2-morpholino-5-((1H)-1,2,4-triazol-5-yl)thiophene-3-carbonitrile
• 英文别名: 4-(4-cyano-2-fluorophenyl)-2-morpholino-5-(1H-1,2,4-triazol-5-yl)thiophene-3-carbonitrile；4-(4-cyano-2-fluorophenyl)-2-morpholin-4-yl-5-(1H-1,2,4-triazol-5-yl)thiophene-3-carbonitrile
• CAS: 1276553-09-3
• 化学式: C₁₈H₁₃FN₆OS
• 分子量: 380.405
• InChiKey: MUENOTXSRZEFJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 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 、 hydrazine hydrate 、 二碘甲烷 、 oxone 、 水 、 溶剂黄146 、 cesium fluoride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 2-甲基四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 5.0h， 生成 4-(4-氰基-2-氟苯基)-2-吗啉-5-(1H-1,2,4-三唑-5-基)噻吩-3-腈
  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

文献信息

• Optimized Method for Treating and Curing Arthritis, Diabetes, Multiple Sclerosis and Other Autoimmune Disease
  申请人：Postrel Richard

  公开号：US20190070166A1

  公开（公告）日：2019-03-07

  The present invention teaches a method, system and process for curing, treating and diagnosing arthritis, diabetes and other related autoimmune diseases. By intercepting and mitigating the disease process at the point of origination prevents the disease from developing and stops the lineage of cells causing disease symptoms. This fundamental system addresses cellular events where the immune reaction is emerging thereby preventing advance of the cascade that feeds the disease. Modulating activity of the errant protein at this initiating point in the immune response blocks the autoimmune cascade and prevents formation of secondary and tertiary effects that will characterize the disease. As the cascade progresses, the number of participating enzymes and pathways compounds so that each progression step further from the initiation point requires increasingly complex therapies. Thus, by treating the primary cause, secondary and tertiary symptoms do not appear. This avoids the side effects observed in multi-faceted approaches presently used to manage the disease symptoms rather than disease causation.
• Development of Scalable Syntheses of Selective PI3K inhibitors
  作者：Qinhua Huang、Paul F. Richardson、Neal W. Sach、Jinjiang Zhu、Kevin K.-C. Liu、Graham L. Smith、Daniel M. Bowles

  DOI：10.1021/op100286g

  日期：2011.5.20

  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.