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Method of utilizing carbonylation reaction to synthesize TNF-alpha inhibitor through one-pot process

A carbonylation reaction, α inhibitor technology, applied in clinical, cell biology, medicine fields, can solve the problem of no effective treatment methods for diseases, and achieve the effects of novel and unique synthesis methods, simple and easy-to-obtain raw materials, and mild reaction conditions

Inactive Publication Date: 2017-10-10
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Rheumatoid Arthritis (RA) is an autoimmune disease with a high incidence rate, and there is currently no effective treatment for this disease

Method used

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  • Method of utilizing carbonylation reaction to synthesize TNF-alpha inhibitor through one-pot process
  • Method of utilizing carbonylation reaction to synthesize TNF-alpha inhibitor through one-pot process
  • Method of utilizing carbonylation reaction to synthesize TNF-alpha inhibitor through one-pot process

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add 0.2 mmoles of benzaldehyde, 0.2 mmoles of 2,6-diisopropylaniline, 0.01 mmoles of palladium dichlorodiacetonitrile, 0.2 mmoles of copper oxide into a 25 mL test tube, add toluene (PhMe) and N,N- Dimethylformamide (DMF) was used as a mixed solvent with a volume ratio of 10:1, and stirred at room temperature for 12 hours. Then put on a balloon containing carbon monoxide and oxygen gas (volume ratio 1:1) as a carbonyl source, and stir at 100 degrees Celsius for 48 hours. After the TLC (thin layer chromatography) detection reaction, the reaction solution was cooled to room temperature, the balloon was removed, and the unreacted carbon monoxide and oxygen were slowly vented. The reaction solution was filtered, the filtrate was decompressed and rotary evaporated to remove the solvent, and then separated and purified by column chromatography to obtain the target product TNF-α inhibitor. The eluent of the column chromatography used was petroleum ether: ethyl acetate with a v...

Embodiment 2

[0029] Add 0.2 mmoles of benzaldehyde, 0.2 mmoles of 2,6-diisopropylaniline, 0.01 mmoles of palladium dichlorodiacetonitrile, 0.2 mmoles of copper oxide into a 25 mL test tube, add toluene (PhMe) as a solvent, and Stirring was continued for 12 hours. Then put on a balloon containing carbon monoxide and oxygen gas (volume ratio 1:1) as a carbonyl source, and stir at 100 degrees Celsius for 48 hours. TLC (thin layer chromatography) tracking detection, no target product was detected.

Embodiment 3

[0031] Add 0.2 mmol of benzaldehyde, 0.2 mmol of 2,6-diisopropylaniline, 0.01 mmol of dichlorodiacetonitrile palladium, 0.2 mmol of copper oxide, and add N,N-dimethylformamide to a 25 mL test tube. (DMF) was used as a solvent, and stirred at room temperature for 12 hours. Then put on a balloon containing carbon monoxide and oxygen gas (volume ratio 1:1) as a carbonyl source, and stir at 100 degrees Celsius for 48 hours. TLC (thin layer chromatography) tracking detection, no target product was detected.

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Abstract

The invention relates to a method of utilizing carbonylation reaction to synthesize TNF-alpha inhibitor through a one-pot process. The method includes: using benzaldehyde and 2, 6-diisopropyl aniline as reaction raw materials; performing amine-aldehyde condensation and oxidative carbonylation to synthesize the TNF-alpha inhibitor through the one-pot process. The method is mild in reaction condition, the raw materials are simple and easy to obtain, and a target product can be constructed by carbonylation reaction through the one-pot process, so that synthesis means is novel and unique.

Description

technical field [0001] The invention relates to the technical fields of medicine, clinic, cell biology and the like, and in particular relates to a new synthetic method for synthesizing TNF-α inhibitors by utilizing carbonylation reaction in one pot. Background technique [0002] Rheumatoid Arthritis (RA) is an autoimmune disease with a high incidence rate, and there is currently no effective treatment for this disease. As a pro-inflammatory cell molecule, TNF-α plays a very important role in the pathogenesis of RA. Therefore, with the continuous development of biological agents, the use of TNF-α inhibitors in the clinical treatment of RA has been more and more applied. It is precisely because of these application characteristics of TNF-α inhibitors that the synthesis of TNF-α inhibitors has become a research hotspot in the field of new drug development. We synthesized a TNF-α inhibitor in a one-pot method using carbonylation reaction, and its synthetic route is as follows...

Claims

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Application Information

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IPC IPC(8): C07D209/48
CPCC07D209/48
Inventor 江焕峰及方华伍婉卿
Owner SOUTH CHINA UNIV OF TECH
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