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Synthesis method of Fenbufen

A synthesis method and compound technology, applied in chemical instruments and methods, pharmaceutical formulations, drug combinations, etc., can solve problems such as low product yield, complicated post-treatment purification process, and mild reaction conditions, and achieve reaction and post-treatment purification Simple process, high reaction regioselectivity and yield, and mild reaction conditions

Active Publication Date: 2019-10-15
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, in the existing synthetic methods of fenbufen, there are generally many synthetic steps, poor reaction regioselectivity, low product yield, mild reaction conditions, complicated reaction and post-treatment purification process, etc.

Method used

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  • Synthesis method of Fenbufen
  • Synthesis method of Fenbufen
  • Synthesis method of Fenbufen

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] (1) Under an inert atmosphere, mix 0.01mmol allylpalladium(II) chloride dimer, 0.2mmol 2-(dicyclohexylphosphono)-1-phenyl-1H-pyrrole, 1mmol N-(octa Aminoquinoline) but-3-enamide, 5mmol lithium acetate, 3mmol 4-bromobiphenyl, 3mmol cyanoacetic acid, and 100mmol water were mixed, and 0.1mmol of the mixed material and 1mL of anhydrous 2,3-butanediol were added to the reaction vessel Mix well in the medium, place the reaction vessel in an oil bath at 125°C and stir vigorously for 12 hours, and purify the reaction product through a silica gel column (flushing the chromatography silica gel column with petroleum ether at a ratio of ethyl acetate 1:20), to obtain Group compounds;

[0024] (2) 1 mmol of the compound is added to 50 mmol of ethanol solvent containing 1.5 mmol of sodium hydroxide, and the mixture is heated to 130° C. for reflux for 12 hours, and the reaction product is distilled under reduced pressure (the pressure of the reduced pressure distillation is within 100...

Embodiment 2

[0028] (1) Under an inert atmosphere, mix 0.1mmol allylpalladium(II) chloride dimer, 0.02mmol 2-(dicyclohexylphosphono)-1-phenyl-1H-pyrrole, 1mmol N-(octa Aminoquinoline) but-3-enamide, 1mmol lithium acetate, 1)mmol 4-bromobiphenyl, 1mmol cyanoacetic acid and 1mmol water were mixed, and 0.1mmol mixed material and 1mL anhydrous 2,3-butanediol were added to Mix well in the reaction vessel, place the reaction vessel in an oil bath at 125°C and vigorously stir the reaction for 12 hours, and purify the reaction product through a silica gel column (flush the chromatographic silica gel column with petroleum ether at a ratio of ethyl acetate 1:20), to obtain Compounds with directing groups;

[0029] (2) 1mmol of the compound is added to 5mmol ethanol solvent containing 4mmol sodium hydroxide, and the mixture is heated to 140°C for 12 hours under reflux, and the reaction product is subjected to underpressure distillation (the pressure of underpressure distillation is within 100mbar, th...

Embodiment 3

[0033] (1) Under an inert atmosphere, mix 0.05mmol allylpalladium(II) chloride dimer, 0.1mmol 2-(dicyclohexylphosphono)-1-phenyl-1H-pyrrole, 1mmol N-(octa Aminoquinoline) but-3-enamide, 3mmol lithium acetate, 2mmol 4-bromobiphenyl, 2mmol cyanoacetic acid, and 50mmol water were mixed, and 0.1mmol of the mixed material and 1mL of anhydrous 2,3-butanediol were added to the reaction vessel Mix well in the medium, place the reaction vessel in an oil bath at 125°C and stir vigorously for 12 hours, and purify the reaction product through a silica gel column (flushing the chromatography silica gel column with petroleum ether at a ratio of ethyl acetate 1:20), to obtain Group compounds;

[0034] (2) 1 mmol of the compound is added to 30 mmol of ethanol solvent containing 2.5 mmol of sodium hydroxide, and the mixture is heated to 135° C. for reflux for 12 hours, and the reaction product is subjected to underpressure distillation (the pressure of underpressure distillation is within 100 ...

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Abstract

The invention discloses a synthesis method of Fenbufen. The synthesis method comprises the following steps: uniformly mixing raw materials of N-(oct-aminoquinoline) butyl-3-enamide, 4-bromobiphenyl and so on with anhydrous 2, 3-butanediol and performing a drastic stirring reaction on the mixture in an oil bath at the temperature of 125-135 DEG C for 12h, so as to obtain a compound with a guiding group; adding the compound into an ethanol solvent containing sodium hydroxide for heating reflux, so as to obtain biphenyl butyrate; mixing biphenyl butyrate, p-toluenesulfonic acid and methanol for heating reflux, so as to obtain biphenyl methyl butyrate; adding biphenyl methyl butyrate and potassium peroxomonosulfate into nitromethane, then adding potassium bromide, performing a reaction at thetemperature of 50 DEG C, adding sodium hydroxide for reflux acidification, so as to obtain Fenbufen. According to the synthesis method, the problem that a synthesis process of the existing Fenbufen has excessive steps is effectively solved; additionally, the synthesis method has the characteristics of being high in reaction regioselectivity and yield, mild in reaction conditions and simple in reaction and aftertreatment purification processes.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, in particular to a method for synthesizing fenbufen. Background technique [0002] The chemical name of fenbufen is 3-(4-biphenylcarbonyl)propionic acid, white or off-white needle crystals. Long-acting non-steroidal anti-inflammatory analgesics. Its mechanism of action is to inhibit prostaglandin synthesis. For rheumatoid arthritis, osteoarthritis, ankylosing spondylitis and gout embolism. [0003] However, in the existing synthetic methods of fenbufen, there are generally problems such as many synthetic steps, poor reaction regioselectivity, low product yield, mild reaction conditions, and complicated reaction and post-treatment purification processes. Contents of the invention [0004] The primary purpose of the present invention is to provide a synthetic method for fenbufen, which aims to solve the problems in the prior art in the above-mentioned background art. [0005] The pr...

Claims

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Application Information

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IPC IPC(8): C07C67/00C07C69/616C07C67/313C07C69/738C07C51/09C07C59/84C07D215/40A61K31/192A61P29/00
CPCC07C67/00C07C67/313C07C51/09C07D215/40A61K31/192A61P29/00C07C69/616C07C69/738C07C59/84
Inventor 吴晓进郑可旺
Owner NANJING UNIV OF TECH
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