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Method of preparing eszopiclone intermediate 6-(5-chloro-2-pyridyl)-5,7-dioxy-6,7-dihydro-5H-pyrrolo[3,4-b] pyrazine

A technology for eszopiclone and intermediates, which is applied in the field of preparation of intermediates for the anti-insomnia drug eszopiclone, and can solve problems such as purchase and use restrictions

Active Publication Date: 2007-10-24
JIANGSU TASLY DIYI PHARMA CO LTD +1
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  • Description
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  • Application Information

AI Technical Summary

Problems solved by technology

Acetic anhydride is a precursor drug whose purchase and use are highly restricted

Method used

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  • Method of preparing eszopiclone intermediate 6-(5-chloro-2-pyridyl)-5,7-dioxy-6,7-dihydro-5H-pyrrolo[3,4-b] pyrazine
  • Method of preparing eszopiclone intermediate 6-(5-chloro-2-pyridyl)-5,7-dioxy-6,7-dihydro-5H-pyrrolo[3,4-b] pyrazine
  • Method of preparing eszopiclone intermediate 6-(5-chloro-2-pyridyl)-5,7-dioxy-6,7-dihydro-5H-pyrrolo[3,4-b] pyrazine

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Experimental program
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Effect test

Embodiment 1

[0016] Under the protection of dry nitrogen, chloroform (560mL), 3-(5-chloropyridine-2-amino)formylpyrazine-2-carboxylic acid (II, 55.7g, 0.2mol), diiso Propylamine (23.3g, 0.23mol), stirred to dissolve. The temperature was lowered to -20°C, methyl chloroformate (23.87 g, 0.22 mol) was added dropwise, samples were taken every half hour for HPLC monitoring, and the reaction was terminated until the raw material content was <1%.

[0017] The reaction solution was washed with hydrochloric acid (10% 150 mL×2), water (200 mL×3). The organic phase was separated, dried with anhydrous sodium sulfate (4g) for 4h, and activated carbon (5g) was decolorized at room temperature for 2h. Suction filtration, concentration under reduced pressure to remove all solvents, to obtain 50.5 g of off-white solid, yield 96.9%, HPLC content 98.5%. mp239~241℃. 1 H NMR (CDCl 3 , 300MHz), δ: 9.06(s, 2H, ArH), 8.67(d, 1H, PyH, J=2.58Hz), 7.93(dd, 1H, J=8.46Hz & 2.52Hz, PyH), 7.49(d, 1H, 8.52Hz, PyH). (...

Embodiment 2

[0019] Reaction solvent is benzene, and all the other are with embodiment 1.

[0020] Yield 95%, content 99%.

Embodiment 3

[0022] Reaction solvent is toluene, and carboxyl activator is ethyl chloroformate, and all the other are with embodiment 1.

[0023] Yield 93%, content 98%.

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Abstract

The invention discloses a making method of 6-(5-chlorine-2-pyridine)-5,7-dioxy-6,7-dihydrogen-5H-pyrrole [3,4-b] pyrazine (I) as intermediate of right-adjuvant clone, which comprises the following steps: dissolving 3-(5-chloropyridine-2-amino)formyl morpholine pyrazine-2-carboxyl acid (II) into the composite liquid of organic solvent / amine; adding chloroformate in the reacting liquid; obtaining the product I.

Description

technical field [0001] The invention relates to a method for preparing an intermediate of the anti-insomnia drug eszopiclone, in particular to a method for preparing the compound 6-(5-chloro-2-pyridyl)-5,7-dioxo-6,7 - The method of dihydro-5H-pyrrolo[3,4-b]pyrazine (I). Background technique [0002] Drugs clinically used for the treatment of insomnia mainly include barbiturates (first generation), benzodiazepines (second generation), non-benzodiazepines (third generation) and traditional Chinese medicines. The market of first-generation and second-generation anti-insomnia drugs shows a clear downward trend due to the large side effects and the tendency to generate dependence and tolerance. The third-generation non-benzodiazepine hypnotics can selectively act on BZ1 receptors, and the residual effects produced are relatively small. The phenomenon of "sleeping" is rarely produced in the next morning, and does not affect the mental activity and al...

Claims

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Application Information

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IPC IPC(8): C07D487/04
Inventor 彭久合陈昊张广明
Owner JIANGSU TASLY DIYI PHARMA CO LTD
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