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A kind of synthetic method of fenbufen

A synthesis method and compound technology, applied in chemical instruments and methods, drug combinations, pharmaceutical formulations, etc., can solve the problems of low product yield, complicated post-treatment purification process, and many synthesis steps, and achieve reaction and post-treatment purification process Simple, regioselective and high yield, solve the effect of too many steps

Active Publication Date: 2021-09-10
NANJING TECH UNIV
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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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  • A kind of synthetic method of fenbufen
  • A kind of synthetic method of fenbufen
  • A kind of synthetic 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 present invention mixes raw materials such as N-(octaaminoquinoline) but-3-enamide, 4-bromobiphenyl and anhydrous 2,3-butanediol under an inert atmosphere and then heats the oil at 125-135°C. Vigorously stirring and reacting in the bath for 12 hours, a compound with a directing group was obtained; the compound was added to an ethanol solvent containing sodium hydroxide and heated to reflux to obtain biphenylbutyric acid; biphenylbutyric acid, p-toluenesulfonic acid, Mix methanol and heat to reflux to obtain methyl biphenyl butyrate; add methyl biphenyl butyrate and potassium peroxymonosulfonate to nitromethane, then add potassium bromide, react at 50°C, and add hydroxide Sodium reflux acidification to obtain fenbufen. The invention effectively solves the problem of too many steps in the existing fenbufen synthesis process, and has the characteristics of high reaction regioselectivity and yield, mild reaction conditions, and simple reaction and post-treatment purification process.

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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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/00C07C69/616C07C67/313C07C69/738C07C51/09C07C59/84C07D215/40A61K31/192A61P29/00
CPCA61K31/192A61P29/00C07C51/09C07C67/00C07C67/313C07D215/40C07C69/616C07C69/738C07C59/84
Inventor 吴晓进郑可旺
Owner NANJING TECH UNIV
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