N-(3-bromo-6-methylpyridin-2-yl)acetamide | 875051-78-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(3-bromo-6-methylpyridin-2-yl)acetamide
• 英文别名: 6-acetamido-5-bromo-2-methylpyridine；N-(3-bromo-6-methyl-pyridin-2-yl)-acetamide；N-(3-bromo-6-methylpyridin-2-yl)-acetamide
• CAS: 875051-78-8
• 化学式: C₈H₉BrN₂O
• 分子量: 229.076
• InChiKey: GNRKGLSYIBFJLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-bromo-6-methylpyridin-2-yl)acetamide 在 potassium dihydrogenphosphate 、 sodium permanganate 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  Discovery and Optimization of Selective Na_v1.8 Modulator Series That Demonstrate Efficacy in Preclinical Models of Pain

  摘要：

  Voltage-gated sodium channels, in particular Na(v)1.8, can be targeted for the treatment of neuropathic and inflammatory pain. Herein, we described the optimization of Na(v)1.8 modulator series to deliver subtype selective, state, and use-dependent chemical matter that is efficacious in preclinical models of neuropathic and inflammatory pain.

  DOI：

  10.1021/acsmedchemlett.5b00059
• 作为产物：
  描述：

  乙酸酐 、 2-氨基-3-溴-6-甲基吡啶 在 碳酸氢钠 、 水 、 二氯甲烷 、 magnesium sulfate 、 silica gel 、 乙酸乙酯 、 正庚烷 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以heptane, 75:25, afforded the title compound as a white solid in 75% yield, 9.2 g的产率得到N-(3-bromo-6-methylpyridin-2-yl)acetamide
  参考文献：
  名称：

  Pyridine derivatives

  摘要：

  本发明涉及式(I)的化合物及其药学上可接受的盐和溶剂化物，制备这些化合物的方法、制备中间体的方法、含有这些化合物的组合物及这些化合物用于治疗疼痛的用途。

  公开号：

  US07649004B2

文献信息

• Pyridine Derivatives
  申请人：Lane Charlotte Alice Louise

  公开号：US20080312235A1

  公开（公告）日：2008-12-18

  The present invention relates to compounds of the formula (I) and pharmaceutically acceptable salts and solvates thereof, to processes for the preparation of, intermediates used in the preparation of, and compositions containing such compounds and the uses of such compounds for the treatment of pain.

  本发明涉及式(I)的化合物及其药学上可接受的盐和溶剂化物，制备过程中使用的中间体，含有这种化合物的组合物以及这种化合物用于治疗疼痛的用途。
• Pyridine Derivatives as Sodium Channel Modulators
  申请人：Gibson Karl Richard

  公开号：US20100240652A1

  公开（公告）日：2010-09-23

  The present invention relates to compounds of the formula (I) and pharmaceutically acceptable salts and solvates thereof, to processes for the preparation of, intermediates used in the preparation of, and compositions containing such compounds and the uses of such compounds for the treatment of pain.

  本发明涉及式(I)的化合物及其药学上可接受的盐和溶剂化物，制备这些化合物的方法，制备中使用的中间体，含有这些化合物的组合物以及这些化合物用于治疗疼痛的用途。
• [EN] PYRIDINE DERIVATIVES<br/>[FR] DERIVES DE PYRIDINE
  申请人：PFIZER LTD

  公开号：WO2006011050A3

  公开（公告）日：2006-10-05
• Optimisation of Permanganate Oxidation and Suzuki−Miyaura Coupling Steps in the Synthesis of a Na_v1.8 Sodium Channel Modulator
  作者：M. Jonathan Fray、Adam T. Gillmore、Melanie S. Glossop、David J. McManus、Ian B. Moses、Céline F.B. Praquin、Keith A. Reeves、Lisa R. Thompson

  DOI：10.1021/op900092h

  日期：2010.1.15

  The development is described (if a viable kilo-scale synthesis of the Na(v)1.8 sodium channel modulator, N-methyl-6-amino5-(2,3,5-trichlorophenyl)pyridine-2-carboxamide (PF-1247324) in five steps, starting from 6-amino-5-bromo-2-picoline, in 33% overall yield. Two key steps required significant optimisation to improve yield and reproducibility. Oxidation or 6-acetamido-5-bromo-2-methylpyridine by permanganate to give the corresponding carboxylic acid derivative was improved by adding potassium dihydrogen phosphate, which moderated the reaction mixture pH and doubled the yield. The potassium fluoride-promoted Suzuki-Miyaura coupling between 2,4,5-trichlorophenylboronic acid and methyl 6-amino-5-bromopyridine-2-carboxylate, catalysed by tri(tert-butyl)phosphinepalladium (0), proceeded reliably to completion at room temperature in high yield when water was added. Anhydrous reaction mixtures reacted much more slowly, and 'wet' mixtures led to significant proto-deboronation in the absence of sufficient active catalyst. In the final step, amidation of the ester with methylamine gave PF-1247324.
• WO2007/83239
  申请人：——

  公开号：——

  公开（公告）日：——