3-(4-methoxyphenyl)-1-(p-tolyl)-1H-pyrazol-5-amine | 618092-84-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-methoxyphenyl)-1-(p-tolyl)-1H-pyrazol-5-amine
• 英文别名: 5-amino-3-(4-methoxyphenyl)-1-(p-tolyl)-1H-pyrazole；3-(4-Methoxyphenyl)-1-(4-methylphenyl)-1H-pyrazol-5-amine；5-(4-methoxyphenyl)-2-(4-methylphenyl)pyrazol-3-amine
• CAS: 618092-84-5
• 化学式: C₁₇H₁₇N₃O
• 分子量: 279.341
• InChiKey: CCRAGMOPTBNFNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  53.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyphenyl)-1-(p-tolyl)-1H-pyrazol-5-amine 在 碘苯二乙酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以87%的产率得到(Z)-3-(4-methoxyphenyl)-3-((E)-p-tolyldiazenyl)acrylonitrile
  参考文献：
  名称：

  PIDA-mediated oxidative aromatic C N bond cleavage: Efficient methodology for the synthesis of 1,2-diaza-1,3-dienes under ambient conditions

  摘要：

  DOI：

  10.1016/j.tetlet.2021.153252
• 作为产物：
  描述：

  对甲基苯肼 、 4-甲氧基苯甲酰基乙腈 在 montmorillonite K-10 clay 作用下， 以 异丙醇 为溶剂， 反应 48.0h， 以75%的产率得到3-(4-methoxyphenyl)-1-(p-tolyl)-1H-pyrazol-5-amine
  参考文献：
  名称：

  Potent and Selective Amidopyrazole Inhibitors of IRAK4 That Are Efficacious in a Rodent Model of Inflammation

  摘要：

  IRAK4 is a critical upstream kinase in the IL-1R/TLR signaling pathway. Inhibition of IRAK4 is hypothesized to be beneficial in the treatment of autoimmune related disorders. A screening campaign identified a pyrazole class of IRAK4 inhibitors that were determined by X-ray crystallography to exhibit an unusual binding mode. SAR efforts focused on the identification of a potent and selective inhibitor with good aqueous solubility and rodent pharmacokinetics. Pyrazole C-3 piperidines were well tolerated, with N-sulfonyl analogues generally having good rodent oral exposure but poor solubility. N-Alkyl piperidines exhibited excellent solubility and reduced exposure. Pyrazoles possessing NI pyridine and fluorophenyl substituents were among the most active. Piperazine 32 was a potent enzyme inhibitor with good cellular activity. Compound 32 reduced the in vivo production of proinflammatory cytokines and was orally efficacious in a mouse antibody induced arthritis disease model of inflammation.

  DOI：

  10.1021/acsmedchemlett.5b00106

文献信息

• Vilsmeier reagent-mediated synthesis of 6-[(formyloxy)methyl]-pyrazolopyrimidines via a one-pot multiple tandem reaction
  作者：Shi-Han Lu、Po-Lin Liu、Fung Fuh Wong

  DOI：10.1039/c5ra07707a

  日期：——

  les as the starting material was developed for the efficient synthesis of 6-[(formyloxy)methyl]-1H-pyrazolo[3,4-d]pyrimidine. This new multiple tandem reaction, involving the Vilsmeier–Haack reaction, the Morgan–Walls reaction, sequential elimination, substitution, and final hydrolysis, afforded formyloxymethyl pyrazolo[3,4-d]pyrimidine products in good yields.

  以5-（2-氯乙酰氨基）吡唑为起始原料，开发了一种新的Vilsmeier试剂介导的一锅反应，用于有效合成6-[（（甲酰氧基）甲基] -1 H-吡唑并[3,4- d ]嘧啶。这种新的多级串联反应，包括Vilsmeier-Haack反应，Morgan-Walls反应，顺序消除，取代和最终水解，可提供高收率的甲酰氧基甲基吡唑并[3,4- d ]嘧啶产物。