6,8-difluoro-1-tributylstannanyl-imidazo[1,5-a]pyridine | 1426427-01-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 6,8-difluoro-1-tributylstannanyl-imidazo[1,5-a]pyridine
• 英文别名: 6,8-Difluoro-1-tributylstannyl-imidazo[1,5-a]pyridine；tributyl-(6,8-difluoroimidazo[1,5-a]pyridin-1-yl)stannane
• CAS: 1426427-01-1
• 化学式: C₁₉H₃₀F₂N₂Sn
• 分子量: 443.167
• InChiKey: OXVOUKDGNVSBQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.67
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  17.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((S)-2-methoxy-1-methyl-ethyl)-amide 、 6,8-difluoro-1-tributylstannanyl-imidazo[1,5-a]pyridine 在 四(三苯基膦)钯 、 碘化亚铜 水 、 乙醚 、 Brine 、 Sodium sulfate-III 、 silica gel 、 methanol-dichloromethane 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以to afford 136 mg (89%) of 2-(6,8-difluoro-imidazo[1,5-a]pyridin-1-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((S)-2-methoxy-1-methyl-ethyl)-amide as a yellow solid的产率得到2-(6,8-difluoro-imidazo[1,5-a]pyridin-1-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((S)-2-methoxy-1-methyl-ethyl)-amide
  参考文献：
  名称：

  Pyrrolopyrazine kinase inhibitors

  摘要：

  本发明涉及使用式I中新型吡咯吡嗪衍生物，其中变量如本文所述，其抑制JAK和SYK并且用于治疗自身免疫和炎症性疾病。

  公开号：

  US08658646B2
• 作为产物：
  描述：

  N-((3,5-difluoro-pyridin-2-yl)-methyl)-formamide 在 碘 、 碳酸氢钠 、 isopropyl magnesium chloride 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， 生成 6,8-difluoro-1-tributylstannanyl-imidazo[1,5-a]pyridine
  参考文献：
  名称：

  Strategic use of conformational bias and structure based design to identify potent JAK3 inhibitors with improved selectivity against the JAK family and the kinome

  摘要：

  Using a structure based design approach we have identified a series of indazole substituted pyrrolopyrazines, which are potent inhibitors of JAK3. Intramolecular electronic repulsion was used as a strategy to induce a strong conformational bias within the ligand. Compounds bearing this conformation participated in a favorable hydrophobic interaction with a cysteine residue in the JAK3 binding pocket, which imparted high selectivity versus the kinome and improved selectivity within the JAK family. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2013.02.012

文献信息

• [EN] PYRROLOPYRAZINE KINASE INHIBITORS<br/>[FR] INHIBITEURS DE PYRROLOPYRAZINE KINASE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2013030138A1

  公开（公告）日：2013-03-07

  The present invention relates to the use of novel pyrrolopyrazine derivatives of Formula I, wherein the variables are defined as described herein, which inhibit JAK and SYK and are useful for the treatment of auto-immune and inflammatory diseases.

  本发明涉及式I的新型吡咯并吡嗪衍生物的使用，其中变量如本文所述定义，其抑制JAK和SYK，并可用于治疗自身免疫和炎症性疾病。
• PYRROLOPYRAZINE KINASE INHIBITORS
  申请人：Chen Shaoqing

  公开号：US20130059834A1

  公开（公告）日：2013-03-07

  The present invention relates to the use of novel pyrrolopyrazine derivatives of Formula I, wherein the variables are defined as described herein, which inhibit JAK and SYK and are useful for the treatment of auto-immune and inflammatory diseases.

  本发明涉及使用新型吡咯吡嗪衍生物（式I）的使用，其中变量如此处所述，其抑制JAK和SYK并且适用于治疗自身免疫和炎症性疾病。
• Strategic use of conformational bias and structure based design to identify potent JAK3 inhibitors with improved selectivity against the JAK family and the kinome
  作者：Stephen M. Lynch、Javier DeVicente、Johannes C. Hermann、Saul Jaime-Figueroa、Sue Jin、Andreas Kuglstatter、Hongju Li、Allen Lovey、John Menke、Linghao Niu、Vaishali Patel、Douglas Roy、Michael Soth、Sandra Steiner、Parcharee Tivitmahaisoon、Minh Diem Vu、Calvin Yee

  DOI：10.1016/j.bmcl.2013.02.012

  日期：2013.5

  Using a structure based design approach we have identified a series of indazole substituted pyrrolopyrazines, which are potent inhibitors of JAK3. Intramolecular electronic repulsion was used as a strategy to induce a strong conformational bias within the ligand. Compounds bearing this conformation participated in a favorable hydrophobic interaction with a cysteine residue in the JAK3 binding pocket, which imparted high selectivity versus the kinome and improved selectivity within the JAK family. (C) 2013 Published by Elsevier Ltd.
• Pyrrolopyrazine kinase inhibitors
  申请人：Chen Shaoqing

  公开号：US08658646B2

  公开（公告）日：2014-02-25

  The present invention relates to the use of novel pyrrolopyrazine derivatives of Formula I, wherein the variables are defined as described herein, which inhibit JAK and SYK and are useful for the treatment of auto-immune and inflammatory diseases.

  本发明涉及使用式I中新型吡咯吡嗪衍生物，其中变量如本文所述，其抑制JAK和SYK并且用于治疗自身免疫和炎症性疾病。