[6-tert-butylamino-1-(tetrahydropyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-3-yl]methyl benzyl ether | 1173989-74-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并吡啶类
• 英文名称: [6-tert-butylamino-1-(tetrahydropyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-3-yl]methyl benzyl ether
• 英文别名: N-tert-butyl-1-(oxan-2-yl)-3-(phenylmethoxymethyl)pyrazolo[3,4-b]pyridin-6-amine
• CAS: 1173989-74-6
• 化学式: C₂₃H₃₀N₄O₂
• 分子量: 394.517
• InChiKey: JBTCLAQCKHQZBC-UHFFFAOYSA-N

物化性质

• 熔点：
  69-70 °C
• 沸点：
  557.7±50.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  61.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [6-tert-butylamino-1-(tetrahydropyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-3-yl]methyl benzyl ether 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、68.95 kPa 条件下， 反应 18.0h， 以95%的产率得到[6-tert-butylamino-1-(tetrahydropyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-3-yl]methanol
  参考文献：
  名称：

  Development of practical syntheses of potent non-nucleoside reverse transcriptase inhibitors

  摘要：

  The development of practical and efficient syntheses of the potent non-nucleoside reverse transcriptase inhibitors I and 2 is described. The preparation of I proceeded in four synthetic steps and in 48% overall yield from 3. The long-term synthesis of 2 proceeded in nine synthetic steps and in 47% overall yield from commercially available 2,6-diflurorpyridine. The route to 2 was highlighted by the three-step synthesis of intermediate 22 and the high yielding coupling between 18 and phenol 8. The overall sequence required no chromatography and has successfully been utilized for the manufacture of 2 on large scale. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2009.03.084
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 (3-benzyloxymethyl-1H-pyrazolo[3,4-b]pyridin-6-yl)tert-butylamine 在 4-甲基苯磺酸吡啶 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以99.1 g的产率得到[6-tert-butylamino-1-(tetrahydropyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-3-yl]methyl benzyl ether
  参考文献：
  名称：

  Development of practical syntheses of potent non-nucleoside reverse transcriptase inhibitors

  摘要：

  The development of practical and efficient syntheses of the potent non-nucleoside reverse transcriptase inhibitors I and 2 is described. The preparation of I proceeded in four synthetic steps and in 48% overall yield from 3. The long-term synthesis of 2 proceeded in nine synthetic steps and in 47% overall yield from commercially available 2,6-diflurorpyridine. The route to 2 was highlighted by the three-step synthesis of intermediate 22 and the high yielding coupling between 18 and phenol 8. The overall sequence required no chromatography and has successfully been utilized for the manufacture of 2 on large scale. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2009.03.084

文献信息

• Development of practical syntheses of potent non-nucleoside reverse transcriptase inhibitors
  作者：Jeffrey T. Kuethe、Yong-Li Zhong、Mahbub Alam、Anthony D. Alorati、Gregory L. Beutner、Dongwei Cai、Fred J. Fleitz、Andrew D. Gibb、Amude Kassim、Kathleen Linn、Danny Mancheno、Benjamin Marcune、Philip J. Pye、Jeremy P. Scott、David M. Tellers、Bangping Xiang、Nobuyoshi Yasuda、Jingjun Yin、Ian W. Davies

  DOI：10.1016/j.tet.2009.03.084

  日期：2009.6

  The development of practical and efficient syntheses of the potent non-nucleoside reverse transcriptase inhibitors I and 2 is described. The preparation of I proceeded in four synthetic steps and in 48% overall yield from 3. The long-term synthesis of 2 proceeded in nine synthetic steps and in 47% overall yield from commercially available 2,6-diflurorpyridine. The route to 2 was highlighted by the three-step synthesis of intermediate 22 and the high yielding coupling between 18 and phenol 8. The overall sequence required no chromatography and has successfully been utilized for the manufacture of 2 on large scale. (C) 2009 Published by Elsevier Ltd.