5-Methyl-3-(4-methylsulfanyl-phenyl)-pyridin-2-ylamine | 217090-18-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-Methyl-3-(4-methylsulfanyl-phenyl)-pyridin-2-ylamine
• 英文别名: 5-Methyl-3-(4-(methylthio)phenyl)pyridin-2-amine；5-methyl-3-(4-methylsulfanylphenyl)pyridin-2-amine
• CAS: 217090-18-1
• 化学式: C₁₃H₁₄N₂S
• 分子量: 230.334
• InChiKey: IDCQTKRKQASDGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  64.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Methyl-3-(4-methylsulfanyl-phenyl)-pyridin-2-ylamine 在 四氧化锇 、 N-甲基吲哚酮 、 氢溴酸 、 溴 、 sodium nitrite 作用下， 以 丙酮 为溶剂， 生成 2-bromo-5-methyl-3-(4-methylsulfonyl)phenylpyridine
  参考文献：
  名称：

  2-Pyridinyl-3-(4-methylsulfonyl)phenylpyridines: Selective and orally active cyclooxygenase-2 inhibitors

  摘要：

  A series of novel 2-pyridinyl-3-(4-methylsulfonyl)phenylpyridines has been synthesized and evaluated with respect to their ability to inhibit the isozymes of cyclooxygenase, COX-I, and COX-2. Optimum COX-2 activity is observed by introduction of a substituent at C5 of the central pyridine. 5-Chloro-3-(4-methylsulfonyl)phenyl-2-(2-methyl-5-pyridinyl)pyridine 33 was identified as the optimum compound in this series. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00499-5
• 作为产物：
  描述：

  4-甲硫基苯硼酸 、 2-氨基-3-溴-5-甲基吡啶 在 四(三苯基膦)钯 sodium carbonate 作用下， 以 乙醇 、 苯 为溶剂， 生成 5-Methyl-3-(4-methylsulfanyl-phenyl)-pyridin-2-ylamine
  参考文献：
  名称：

  2-Pyridinyl-3-(4-methylsulfonyl)phenylpyridines: Selective and orally active cyclooxygenase-2 inhibitors

  摘要：

  A series of novel 2-pyridinyl-3-(4-methylsulfonyl)phenylpyridines has been synthesized and evaluated with respect to their ability to inhibit the isozymes of cyclooxygenase, COX-I, and COX-2. Optimum COX-2 activity is observed by introduction of a substituent at C5 of the central pyridine. 5-Chloro-3-(4-methylsulfonyl)phenyl-2-(2-methyl-5-pyridinyl)pyridine 33 was identified as the optimum compound in this series. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00499-5

文献信息

• PROCESS FOR CYCLOOXYGENASE-2 SELECTIVE INHIBITOR
  申请人：Shah Dharmesh Mahendra

  公开号：US20130245272A1

  公开（公告）日：2013-09-19

  The present invention describes a process for preparing a cyclooxygenase-2 selective inhibitor. It provides a synthetic procedure for the said substance namely 5-chloro-3-(4-methylsulphonyl)phenyl-2-(2-methyl-5-pyridinyl)pyridine of formula (I). The invention also relates to preparation of a new intermediate of formula (IV) and a process to prepare it. Furthermore, the invention describes a process for preparing another key intermediate of formula (II). Compounds of formula (IV) and formula (II) are useful intermediates in synthesis of the said cyclooxygenase-2 inhibitor.

  本发明描述了一种制备环氧合酶-2选择性抑制剂的方法。它提供了一种合成所述物质即式(I)的过程，即5-氯-3-(4-甲基磺酰基)苯基-2-(2-甲基-5-吡啶基)吡啶。本发明还涉及制备式(IV)的新中间体及其制备方法。此外，本发明还描述了一种制备式(II)的另一个关键中间体的方法。式(IV)和式(II)的化合物是合成所述环氧合酶-2抑制剂的有用中间体。