5-Chloro-1-(5-methanesulfonyl-pyridin-2-yl)-3-trifluoromethyl-1H-pyrazole-4-carbaldehyde oxime | 677029-68-4

• 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-Chloro-1-(5-methanesulfonyl-pyridin-2-yl)-3-trifluoromethyl-1H-pyrazole-4-carbaldehyde oxime
• CAS: 677029-68-4
• 化学式: C₁₁H₈ClF₃N₄O₃S
• 分子量: 368.724
• InChiKey: FEZAUEXGRZHEIH-UHFFFAOYSA-N

物化性质

• 沸点：
  529.4±50.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.15
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  97.44
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-Chloro-1-(5-methanesulfonyl-pyridin-2-yl)-3-trifluoromethyl-1H-pyrazole-4-carbaldehyde oxime 在 potassium fluoride 、 三乙胺 、 三氯乙酰氯 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 5-(cyclopentylmethoxy)-1-(5-(methylsulfonyl)pyridin-2-yl)-3-(trifluoromethyl)-1H-pyrazole-4-carbonitrile
  参考文献：
  名称：

  5-Heteroatom-substituted pyrazoles as canine COX-2 inhibitors: Part 2. Structure–activity relationship studies of 5-alkylethers and 5-thioethers

  摘要：

  Structure-activity relationship (SAR) studies of novel 2-[3-trifluoromethyl-5-alky](thio)ether pyrazo-1-yl]-5-methanesulfonyl pyridine derivatives for canine COX enzymes are described. The 4-cyano-5-alkyl ethers were found to have excellent potency and selectivity, whereas the 5-thioethers were potent but less selective than the ether analogs in a canine whole blood, (CWB) COX-2 assay. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.11.110
• 作为产物：
  描述：

  5-Chloro-1-(5-Methanesulfonyl-Pyridin-2-yl)-3-Trifluoromethyl-1H-Pyrazole-4-Carbaldehyde 在 盐酸羟胺 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 2.0h， 以90%的产率得到5-Chloro-1-(5-methanesulfonyl-pyridin-2-yl)-3-trifluoromethyl-1H-pyrazole-4-carbaldehyde oxime
  参考文献：
  名称：

  有效合成5-烷基氨基和硫醚取代的吡唑

  摘要：

  1-（4-甲基磺酰基-2-吡啶基）-5-氯吡唑在4位上与胺亲核试剂和硫醇的亲核取代反应在温和条件下发生，以高收率提供5-烷基氨基和硫醚吡唑。

  DOI：

  10.1016/j.tetlet.2003.08.054

文献信息

• Efficient fluoride-mediated synthesis of 5-alkyl amino- and ether-substituted pyrazoles
  作者：Andrei Shavnya、Subas M. Sakya、Martha L. Minich、Bryson Rast、Kristin Lundy DeMello、Burton H. Jaynes

  DOI：10.1016/j.tetlet.2005.08.022

  日期：2005.10

  Fluoride-mediated nucleophilic substitution reactions of 1-(4-methylsulfonyl (or sulfonamido)-2-pyridyl)-5-chloro-4-cyano pyrazoles with various amines and alcohols occur under mild conditions to provide the 5-alkyl amino and ether pyrazoles in moderate to high yields.

  1-（4-甲基磺酰基（或磺酰胺基）-2-吡啶基）-5-氯-4-氰基吡唑与各种胺和醇的氟化物介导的亲核取代反应在温和条件下发生，以提供5-烷基氨基和醚吡唑中等至高产。
• 5-Heteroatom substituted pyrazoles as canine COX-2 inhibitors. Part 1: Structure–activity relationship studies of 5-alkylamino pyrazoles and discovery of a potent, selective, and orally active analog
  作者：Subas M. Sakya、Kristin M. Lundy DeMello、Martha L. Minich、Bryson Rast、Andrei Shavnya、Robert J. Rafka、David A. Koss、Hengmiao Cheng、Jin Li、Burton H. Jaynes、Carl B. Ziegler、Donald W. Mann、Carol F. Petras、Scott B. Seibel、Annette M. Silvia、David M. George、Lisa A. Lund、Suzanne St. Denis、Anne Hickman、Michelle L. Haven、Michael P. Lynch

  DOI：10.1016/j.bmcl.2005.10.006

  日期：2006.1

  Structure-activity relationship (SAR) studies of the novel 2-[3-di and trifluoromethyl-5-alkylamino pyrazo-1-yl]-5-methanesulfonyl (SO2Me)/sulfamoyl (SO2NH2)-pyridine derivatives for canine COX enzymes are described. The studies led to the identification of 2e as lead with potent in vitro activity, selectivity, and in vivo activity in dogs and cats. (c) 2005 Elsevier Ltd. All rights reserved.