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Synthetic method of rilpivirine intermediate

A technology of rilpivirine and a synthesis method, which is applied in the field of synthesis of rilpivirine intermediates, can solve the problems of high synthesis energy consumption, high cost, environmental pollution and the like, and achieves high raw material utilization rate, high yield, and synthesis process. simple effect

Active Publication Date: 2020-06-26
WUHAN INSTITUTE OF TECHNOLOGY
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Problems solved by technology

[0007] In view of this, the present invention aims to propose a synthetic method of a rilpivirine intermediate, to solve the problems of high energy consumption and high cost, and easy environmental pollution of the existing rilpivirine intermediate

Method used

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  • Synthetic method of rilpivirine intermediate

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Embodiment 1

[0027] A synthetic technique for a rilpivirine intermediate, specifically comprising the following steps:

[0028] 1) Synthesis of 4-amino-3,5-dimethylbenzaldehyde: add 13.5g (0.1mol) 2,4,6-trimethylaniline (me-trimethyl aniline), 250mL 5% hydrochloric acid solution, 56.75g (0.25mol) 2,3-dichloro-5,6-dicyanobenzoquinone, stir until fully mixed, heat up to 25°C, and react for 2h. After the reaction, use 250mL of 10% sodium hydroxide solution was used to treat the reaction solution, and then the mixed solution was extracted four times with 50mL of ethyl acetate, separated, and the organic layer was washed with saturated NaHCO 3 , washed once with saturated saline, and then dried with anhydrous sodium sulfate. Finally, the solvent was distilled off under reduced pressure to obtain 14.3 g of 4-amino-3,5-dimethylbenzaldehyde as a waxy solid. After calculation, the yield was The rate is 95.97%, and through nuclear magnetic resonance test, its hydrogen nuclear magnetic resonance spe...

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Abstract

The invention provides a synthetic method of a rilpivirine intermediate. The synthesis method includes: taking 2, 4, 6-trimethylaniline as the raw material to react with 2, 3-dichloro-5, 6-dicyanobenzoquinone (DDQ) in a diluted hydrochloric acid solution to obtain 4-amino-3, 5-dimethyl benzaldehyde, then carrying out Knoevenagel reaction with cyanoacetic acid under the condition that organic alkali serves as the catalyst to obtain 3-(4-amino-3, 5-dimethylphenyl)2-cyanoacrylate, and then carrying out decarboxylation reaction to obtain the intermediate (E)-3-(4-amino-3, 5-dimethylphenyl)acrylonitrile. According to the invention, the raw materials used in the whole synthesis process are cheap and easily available, the raw material utilization rate is high, the synthesis process is simple, thereaction conditions are mild, the intermediate yield is high, and the method is suitable for the requirements of industrial large-scale production. In addition, compared with an original synthetic route, the reagents used in the method are low in toxicity, therefore the method has good environmental protection benefits.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a method for synthesizing a rilpivirine intermediate. Background technique [0002] Rilpivirine (rilpivirine) is a new type of non-nucleoside reverse transcriptase inhibitor (NNRTI) developed by Tibotec of the United States. It is used for the treatment of AIDS and has the advantages of easy synthesis, strong antiviral activity, high oral bioavailability, and safety. Good features. Its chemical name is: [[4-[[4-[(1E)-2-cyanoethylidene]-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]-benzonitrile . The chemical structure is as follows: [0003] [0004] According to literature reports, rilpivirine is mainly synthesized from two key intermediates, namely intermediate (1): (E)-3-(4-amino-3,5-dimethylphenyl)acrylonitrile and intermediate Body (2): 4((4-amino-2-pyrimidinyl)amino)benzonitrile, intermediate (1) undergoes N-alkylation reaction with intermediate (2) after sal...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/30C07C255/42
CPCC07C253/30C07C221/00C07C223/06C07C255/42
Inventor 刘生鹏谢志翰吴晓宇许莉莉熊芸孙国锋丁一刚
Owner WUHAN INSTITUTE OF TECHNOLOGY
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