Synthesis method of pyrazine-2, 3-dicarboxylic acid bis [(5-chloro-pyridine-2-yl)-amide]

A synthesis method, technology of dicarboxylic acid, applied in the direction of organic chemistry etc.

Pending Publication Date: 2022-06-14
JIANGSU TASLY DIYI PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] At present, there is no relevant report on this impurity in the domestic literature. The control of drug impurity profile is an important measure to ensure the safety and effectiveness of drugs, and it is also a key link to improve the quality of domestic drugs. In order to facilitate the process research and quality control of zopiclone Purity impurity reference substance, urgently need to provide a kind of easy, low-cost method for preparing this impurity

Method used

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  • Synthesis method of pyrazine-2, 3-dicarboxylic acid bis [(5-chloro-pyridine-2-yl)-amide]
  • Synthesis method of pyrazine-2, 3-dicarboxylic acid bis [(5-chloro-pyridine-2-yl)-amide]
  • Synthesis method of pyrazine-2, 3-dicarboxylic acid bis [(5-chloro-pyridine-2-yl)-amide]

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Embodiment 1

[0045] Embodiment 1: a kind of synthetic method of pyrazine-2,3-dicarboxylic acid bis[(5-chloro-pyridin-2-yl)-amide]

[0046] 3-(5-Chloropyridine-2-carbamoyl)-2-pyrazinecarboxylic acid (G) (5.57 g, 20 mmol), triethylamine (4.04 g, 40 mmol), EDCI (4.60 g, 24 mmol), HOBt (3.24 g, 24 mmol) was dispersed in dichloromethane (50 ml, 8.98 times the volume of the weight of compound G), and stirred for 10 minutes. 2-Amino-5-chloropyridine (2.57 g, 20 mmol) was added to the reaction mixture, and the reaction was refluxed for 16 hours.

[0047]The reaction mixture was gradually cooled to room temperature, water was added, stirred, and the layers were separated. The aqueous phase was extracted twice with dichloromethane, the organic phases were combined, washed once with saturated brine, dried over magnesium sulfate, and filtered. After the filtrate was concentrated, column chromatography (filling agent: 200-300 mesh silica gel, eluent: petroleum ether---petroleum ether / ethyl acetate=10...

Embodiment 2

[0050] Embodiment 2: A kind of synthetic method of pyrazine-2,3-dicarboxylic acid bis[(5-chloro-pyridin-2-yl)-amide]

[0051] 3-(5-Chloropyridine-2-carbamoyl)-2-pyrazinecarboxylic acid (Compound G) (5.57 g, 20 mmol), triethylamine (4.04 g, 40 mmol), EDCI (4.60 g, 24 mmol), HOBt (3.24 g, 24 mmol) was dispersed in DMF (50 ml, 8.98 times the volume of the weight of compound G) and stirred for 10 minutes. 2-Amino-5-chloropyridine (2.57 g, 20 mmol) was added to the reaction mixture, and the reaction was carried out at 100° C. for 16 hours.

[0052] The reaction mixture was gradually cooled to room temperature, water was added and stirred, then 50 mL of dichloromethane was added to the aqueous phase for extraction twice, the organic phases were combined, the aqueous phase was extracted twice with dichloromethane, the organic phases were combined and washed once with saturated brine, Dry over magnesium sulfate and filter. After the filtrate was concentrated, column chromatography (...

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Abstract

The invention relates to a synthesis method of pyrazine-2, 3-dicarboxylic acid bis [(5-chloro-pyridine-2-yl)-amide], which comprises the following steps: 1) by taking 3-(5-chloropyridine-2-carbamyl)-2-pyrazinecarboxylic acid (compound G) as a raw material, adding triethylamine, EDCI, HOBt and 2-amino-5-chloropyridine into an organic solvent for condensation reaction, and stirring for 4-18 hours; (2) after the reaction is finished, pouring reaction liquid into water, extracting and separating; and (3) purifying the isolate through a purification column to obtain a pyrazine-2, 3-dicarboxylic acid bis [(5-chloro-pyridine-2-yl)-amide] pure product.

Description

technical field [0001] The present invention relates to a method for preparing zopiclone impurities, in particular to a method for preparing pyrazine-2,3-dicarboxylic acid bis[(5-chloro-pyridin-2-yl)-amide]. [0002] technical background [0003] Zopiclone chemical name is 6-(5-chloropyridin-2-yl)-7-[(4-methylpiperazin-1-yl)carbonyloxy]-5,6-dihydropyrrole[ 3.4-b]pyrazin-5-one, a pyrrolidone compound, is the third-generation sedative-hypnotic drug developed by the French Rhone-Poulene Rorer company. It is an inhibitory neurotransmitter γ- Aminobutyric acid (GABA) receptor agonist, with hypnotic, sedative, muscle relaxant, anxiolytic and anticonvulsant effects, mainly used for short-term treatment of insomnia caused by various reasons. [0004] Eszopiclone (Eszopiclone) is a fast-acting, short-acting non-benzodiazepine sedative and hypnotic drug developed by Seprator Company in the United States. It was launched in the United States in April 2005 and belongs to the (S) isomer ...

Claims

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Application Information

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IPC IPC(8): C07D401/14
CPCC07D401/14
Inventor 冀志江丁爱忠孔凯丽徐学宇吴庆丽
Owner JIANGSU TASLY DIYI PHARMA CO LTD
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