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Synthetic method of 3-(pyridine-2-yl-amino) ethyl propionate

A synthetic method, the technology of ethyl propionate, applied in the direction of organic chemistry, etc., can solve problems such as unsuitable for industrial production, unsuitable for industrial production, explosion of ethyl acrylate, etc., achieve low equipment performance requirements, improve production safety, The effect of short reaction times

Inactive Publication Date: 2015-10-14
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Seen from the above-mentioned main synthetic route, compound I is the key intermediate of synthetic compound II, and the synthetic method of compound I mainly contains by 2 aminopyridine and ethyl acrylate by base catalysis (CN1861596A, CN100509799C etc.) and then through column chromatography method to obtain the target product, which is not suitable for industrial production, or under 10-15mmHg, the product is obtained by distillation under reduced pressure, and the final yield is 49.6% (W02012152855A, etc.). The distillation temperature of this method is high, and ethyl acrylate is prone to self-polymerization The reaction is prone to explosion, there are potential safety hazards, and the distillation time is long, which requires high equipment and is not suitable for industrial production

Method used

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  • Synthetic method of 3-(pyridine-2-yl-amino) ethyl propionate
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  • Synthetic method of 3-(pyridine-2-yl-amino) ethyl propionate

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Embodiment 1

[0029] Embodiment 1: synthetic 3-(pyridin-2-ylamino) ethyl propionate

[0030] Add 20.0g of 2-aminopyridine, 276.8ml of ethyl acrylate and 6.36ml of glacial acetic acid to a 100ml three-necked flask in sequence, raise the external temperature to 85°C, and the internal temperature to 80°C, stir overnight, and monitor the reaction by hplc. After 12h, 2-amino Pyridine reaction is complete, lower the system to room temperature, then add 110ml 2N HCl and stir, there is some exotherm during the stirring process, add 50ml ethyl acetate for extraction after 30min, separate liquids, collect the water phase, and then use 50ml ethyl acetate to dilute the water phase Washing, liquid separation, combined water phase, then add 15.8g sodium carbonate solid and 100ml ethyl acetate to extract under stirring, separate liquid to collect organic phase, then use 25ml ethyl acetate to extract water phase, combine organic phase, spin dry ethyl acetate. Then 34g DMF and 170g water were added, stirre...

Embodiment 2

[0031] Embodiment 2: Synthetic 3-(pyridin-2-ylamino) ethyl propionate

[0032] Add 200g of 2-aminopyridine, 276.8ml of ethyl acrylate and 63.6ml of glacial acetic acid to a 1L three-necked flask in sequence, raise the external temperature to 85°C, and the internal temperature to 80°C, stir overnight, and monitor the reaction by hplc. After 12 hours, 2-aminopyridine After the reaction is complete, cool the system down to room temperature, then add 1100ml of 2N HCl and stir. There is some heat generation during the stirring process. After 30 minutes, add 500ml of ethyl acetate for extraction, separate the liquids, collect the water phase, and then wash the water phase with 500ml of ethyl acetate. , liquid separation, combined water phase, then add 158g sodium carbonate solid and 1L ethyl acetate to extract under stirring, separate liquid to collect organic phase, then use 250ml ethyl acetate to extract water phase, combine organic phase, spin dry acetic acid ethyl ester. Then, ...

Embodiment 3

[0033] Embodiment 3: Synthetic 3-(pyridin-2-ylamino) ethyl propionate

[0034]Add 130kg of 2-aminopyridine, 174kg of ethyl acrylate and 44kg of glacial acetic acid to a 2000L three-necked flask in sequence. The external temperature rises to 85°C, and the internal temperature rises to 80°C. Stir overnight, and hplc monitors the reaction. After 12 hours, the reaction of 2-aminopyridine is complete , the system was lowered to room temperature, then added 72L2N HCl and stirred, there was some exotherm during the stirring process, 300min later, 300kg ethyl acetate was added for extraction, the liquid was separated, the water phase was collected, and then the water phase was washed with 300kg ethyl acetate and separated liquid, combined the aqueous phase, and then added 103kg of sodium carbonate solid and 300kg of ethyl acetate under stirring for extraction, separated and collected the organic phase, then extracted the aqueous phase with 150kg of ethyl acetate, combined the organic p...

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Abstract

The invention discloses a synthetic method of 3-(pyridine-2-yl-amino) ethyl propionate. The 3-(pyridine-2-yl-amino) ethyl propionate is obtained by taking 2-aminopyridine and ethyl acrylate as raw materials, performing addition reaction under the catalysis of acetic acid, and performing acid cleaning, alkali dissociation and pulping. The synthetic method disclosed by the invention is safe, simple and convenient to operate, is high in yield, qualified in product purity and high in solvent recovery rate, and is suitable for industrial production.

Description

technical field [0001] The invention relates to the field of pharmaceutical intermediates, in particular to a method for synthesizing the pharmaceutical intermediate 3-(pyridin-2-ylamino) ethyl propionate. Background technique [0002] Ethyl 3-(pyridine-2-amino)propionate (compound I) is a very critical intermediate in the field of medicine. For example, dabigatran etexilate (English name Dabigatranetexilate,) is a new type of direct thrombin inhibitor. The drug was developed by Boehringer Ingelheim of Germany and first launched in Germany and the UK in April 2008. This is the first new class of oral anticoagulant drugs to be marketed in 50 years after warfarin. And 3-[(3-amino-4-methylaminobenzoyl) (pyridin-2-yl) amino] ethyl propionate (compound II) is exactly a key intermediate of synthetic dabigatran etexilate, and 3 Ethyl -(pyridin-2-ylamino)propionate (compound I) is the key raw material for the synthesis of compound II. [0003] [0004] The methods for the synt...

Claims

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Application Information

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IPC IPC(8): C07D213/74
CPCC07D213/74
Inventor 胡文浩王永辉黄海峰丛晓明李新锋刘顺英甘明华
Owner EAST CHINA NORMAL UNIV
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