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Preparation method of dexzopiclone photodegradation impurity

A technology of compound and feeding amount, applied in organic chemistry methods, organic chemistry and other directions, can solve problems such as danger and long route steps, and achieve the effects of low cost, easy operation and mild conditions

Inactive Publication Date: 2020-12-18
迪嘉药业集团股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The shortcoming of this route is: a. route step is longer and needs three-step reaction; b. uses sodium-hydrogen dangerous reagent, and industrialized production has certain danger

Method used

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  • Preparation method of dexzopiclone photodegradation impurity
  • Preparation method of dexzopiclone photodegradation impurity
  • Preparation method of dexzopiclone photodegradation impurity

Examples

Experimental program
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Effect test

Embodiment 1

[0033] Example 1: 6-(5-chloropyridin-2-yl)-6,7-dihydro-5 H -pyrrolo[3,4- b ] Preparation of pyrazin-5-one (compound Ⅰ)

[0034] Add 6-(5-chloropyridin-2-yl)-7-hydroxyl-6,7-dihydro-5 H -pyrrolo[3,4- b ]pyrazin-5-one (compound Ⅱ, 10.00g, 0.0381mol ), 100.0ml toluene, stirred and cooled to -15°C, controlled temperature -15°C, slowly added diisobutylaluminum hydride (11.50ml, 0.0172mol ), after dropping, keep warm at -15°C for 2h. After the reaction is completed, add 50.0ml of methanol dropwise at a temperature below 0°C, stir for 1 hour after the dropwise addition, pour the reaction solution into 1000 ml of 1N hydrochloric acid at 3°C ​​and stir for 1 hour, filter with suction, wash the filtrate with 100.0ml of drinking water, and organically Evaporate to dryness under reduced pressure at a vacuum degree of -0.10MPa in a water bath at 60°C, add 100.0ml of petroleum ether / ethyl acetate (ethyl acetate:petroleum ether=1:5) mixed solution, keep stirring at -10°C for 2h, Suction ...

Embodiment 2

[0036] Add (6-(5-pyridin-2-yl)-5 H -Pyrrole [3,4- b ]pyrazine-5,7(6 H )-diketone (Compound III, 10.00g, 0.0384mol) and 100.0ml of toluene were stirred and cooled to -10~-15°C, and the temperature was controlled at -10°C, and diisobutylaluminum hydride (23.10ml, 0.0346mol) was slowly added dropwise, After dropping, keep warm at -10°C for 2 hours. After the reaction is completed, add 50.0ml of methanol dropwise at a temperature below 0°C, stir for 1 hour after the dropwise addition, pour the reaction solution into 1000 ml of 1N hydrochloric acid at 5°C and stir for 0.5 hours, filter with suction, and wash the filtrate with 100.0ml of drinking water. The organic phase was evaporated to dryness in a water bath at 60°C with a vacuum degree of -0.10MPa, added 100.0ml of petroleum ether / ethyl acetate (ethyl acetate:petroleum ether=1:5) mixed solution, and kept at -10°C to stir and crystallize for 2h , suction filtered, and dried at 50°C to give 6-(5-chloropyridin-2-yl)-6,7-dihydro...

Embodiment 3

[0038] Add 6-(5-chloropyridin-2-yl)-7-hydroxyl-6,7-dihydro-5 H -pyrrolo[3,4- b]Pyrazin-5-one (Compound Ⅱ, 10.00g, 0.0381mol) and 100.0ml xylene were cooled to -12°C with stirring, and diisobutylaluminum hydride (7.70ml, 0.0114mol) was slowly added dropwise under temperature control at -12°C After dropping, keep warm at -12°C for 2h. After the reaction is completed, add 50.0ml of methanol dropwise at a temperature below 0°C, stir for 0.5h after the dropwise addition, pour the reaction solution into 1000ml of 1 N hydrochloric acid at 4°C and stir for 1h, filter with suction, and wash the filtrate with 100.0ml of drinking water , the organic phase was evaporated to dryness in a water bath at 50°C with a vacuum degree of -0.08MPa, added 100.0ml of petroleum ether / ethyl acetate (acetic acid:petroleum ether=1:5) mixed solution, and kept stirring at -5°C for 2h , suction filtered, and dried at 40°C to give 6-(5-chloropyridin-2-yl)-6,7-dihydro-5 H -pyrrolo[3,4- b ] Pyrazin-5-one 8...

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Abstract

The invention relates to a preparation method of a dexzopiclone photodegradable impurity, and belongs to the technical field of chemical synthesis. The invention relates to a preparation method of 6-(5-chloropyridin-2-yl)-6, 7-dihydro-5H-pyrrolo [3, 4-b] pyrazin-5-one (compound I), which is prepared by reacting a compound II or a compound III with diisobutylaluminum hydride under certain conditions. The invention provides a synthetic method of the 6-(5-chloropyridin-2-yl)-6, 7-dihydro-5H-pyrrolo [3, 4-b] pyrazin-5-one (compound I), which is reasonable in process, mild in condition and simple and convenient to operate, and the method is simple to operate and has a certain commercial value.

Description

technical field [0001] The invention relates to a preparation method of (right) zopiclone photodegradation impurities, belonging to the technical field of chemical synthesis. Background technique [0002] . [0003] Zopiclone is a third-generation sedative-hypnotic drug developed by Rhono-Poulene Rorer of France, a non-benzodiazepine hypnotic drug for the treatment of insomnia, which is a spin compound. Eszopiclone is a fast and short-acting non-benzodiazepine sedative-hypnotics developed by Sepracor Corporation of the United States. It is the D-single isomer of zopiclone, with CAS registration number 138729-47-2, and was released in the United States in April 2005. Compared with zopiclone, eszopiclone has stronger curative effect and lower toxicity. [0004] . [0005] 6-(5-Chloropyridin-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one (compound Ⅰ) is (right) zopiclone API It is also the human metabolite after (right) zopiclone enters the body. Therefore, the resea...

Claims

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Application Information

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IPC IPC(8): C07D487/04
CPCC07B2200/07C07D487/04
Inventor 刘彦彬吴艳华刘晓寇磊王大磊张斌
Owner 迪嘉药业集团股份有限公司
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