4-氟-1-[三(1-甲基乙基)硅酯]-1H-吡咯并[2,3-B]吡啶-5-胺 | 685513-93-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 中文名称: 4-氟-1-[三(1-甲基乙基)硅酯]-1H-吡咯并[2,3-B]吡啶-5-胺
• 英文名称: 4-fluoro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-5-ylamine
• 英文别名: 1H-Pyrrolo[2,3-B]pyridin-5-amine, 4-fluoro-1-[tris(1-methylethyl)silyl]-；4-fluoro-1-tri(propan-2-yl)silylpyrrolo[2,3-b]pyridin-5-amine
• CAS: 685513-93-3
• 化学式: C₁₆H₂₆FN₃Si
• 分子量: 307.486
• InChiKey: ZINXVTOHYWMDLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Chloro-5-isopropyl-6-(3-methyl-[1,2,4]oxadiazol-5-yl)-pyrrolo[2,1-f][1,2,4]triazine 、 4-氟-1-[三(1-甲基乙基)硅酯]-1H-吡咯并[2,3-B]吡啶-5-胺 在 N,N-二异丙基乙胺 作用下， 生成
  参考文献：
  名称：

  Discovery and preclinical studies of 5-isopropyl-6-(5-methyl-1,3,4-oxadiazol-2-yl)-N-(2-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (BMS-645737), an in vivo active potent VEGFR-2 inhibitor

  摘要：

  We report herein a series of substituted N-(1H-pyrrolo[2,3-b] pyridin-5-yl) pyrrolo[2,1-f][1,2,4] triazin-4-amines as inhibitors of vascular endothelial growth factor receptor-2 tyrosine kinase. Through structure-activity relationship studies, biochemical potency, pharmacokinetics, and kinase selectivity were optimized to afford BMS-645737 (13), a compound with good preclinical in vivo activity against human tumor xenograft models. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.03.057
• 作为产物：
  描述：

  4-氟-1-[三(1-甲基乙基)硅酯]-1H-吡咯并[2,3-B]吡啶 在 palladium on activated charcoal 氢气 、 仲丁基锂 作用下， 以 四氢呋喃 、 环己烷 、 乙酸乙酯 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 18.92h， 生成 4-氟-1-[三(1-甲基乙基)硅酯]-1H-吡咯并[2,3-B]吡啶-5-胺
  参考文献：
  名称：

  Synthesis of functionalized 7-azaindoles via directed ortho-metalations

  摘要：

  Functionalization at C-5 of 4-fluoro- and 4-chloro-1-triisopropylsilyl-7-azaindole, 1 and 2, respectively, leads to a variety of new substituted 7-azaindole derivatives. We also describe two approaches to introduce functionality at C-6. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.122

文献信息

• Synthesis of functionalized 7-azaindoles via directed ortho-metalations
  作者：Alexandre L’Heureux、Carl Thibault、Réjean Ruel

  DOI：10.1016/j.tetlet.2004.01.122

  日期：2004.3

  Functionalization at C-5 of 4-fluoro- and 4-chloro-1-triisopropylsilyl-7-azaindole, 1 and 2, respectively, leads to a variety of new substituted 7-azaindole derivatives. We also describe two approaches to introduce functionality at C-6. (C) 2004 Elsevier Ltd. All rights reserved.
• Discovery and preclinical studies of 5-isopropyl-6-(5-methyl-1,3,4-oxadiazol-2-yl)-N-(2-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (BMS-645737), an in vivo active potent VEGFR-2 inhibitor
  作者：Réjean Ruel、Carl Thibeault、Alexandre L’Heureux、Alain Martel、Zhen-Wei Cai、Donna Wei、Ligang Qian、Joel C. Barrish、Arvind Mathur、Celia D’Arienzo、John T. Hunt、Amrita Kamath、Punit Marathe、Yueping Zhang、George Derbin、Barri Wautlet、Steven Mortillo、Robert Jeyaseelan、Benjamin Henley、Ravindra Tejwani、Rajeev S. Bhide、George L. Trainor、Joseph Fargnoli、Louis J. Lombardo

  DOI：10.1016/j.bmcl.2008.03.057

  日期：2008.5

  We report herein a series of substituted N-(1H-pyrrolo[2,3-b] pyridin-5-yl) pyrrolo[2,1-f][1,2,4] triazin-4-amines as inhibitors of vascular endothelial growth factor receptor-2 tyrosine kinase. Through structure-activity relationship studies, biochemical potency, pharmacokinetics, and kinase selectivity were optimized to afford BMS-645737 (13), a compound with good preclinical in vivo activity against human tumor xenograft models. (C) 2008 Elsevier Ltd. All rights reserved.