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Process for synthesizing intermediate of (S)-2,6-diamino-4,5,6,7-tetralinbenzothiazole of anti-parkinson drug

An anti-Parkinson and benzothiazole technology, which is applied in the field of drug synthesis technology, can solve the problems of no 4-acetylaminocyclohexanol oxidation report, long reaction cycle, and harmful environment, so as to avoid the use and positioning of highly toxic reagents Good sex, good quality effect

Active Publication Date: 2014-08-27
EASTSKY PHARM ANHUI TECH
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AI Technical Summary

Problems solved by technology

The operation is cumbersome, the reaction cycle is long, and Jones reagent, bromine, HBr and other highly corrosive raw materials are used, which are harmful to the environment
The oxidation of secondary alcohols by TEMPO (tetramethylpiperidine oxide) has been proven to be an effective green process, but there is no report on the oxidation of 4-acetamidocyclohexanol, and the oxidation of TEMPO / DBDMH composite oxidant is more effective is unreported

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0015] (1) Synthesis of p-acetamidocyclohexanone

[0016] Put 100g of 4-acetylaminocyclohexanol into 800ml of acetone and 200ml of water, stir to dissolve, cool down, slowly add 20g of TEMPO / DBDMH composite oxidant, control the reaction temperature below 30°C, keep the reaction for 6 hours after adding, filter, and suction filter until dry . The filtrate was distilled under reduced pressure to recover acetone, and ethyl acetate was added for recrystallization to obtain 96.75 g of p-acetylaminocyclohexanone, with a yield of 98%.

[0017] (2) (±)-2,6-diamino-4,5,6,7-tetrahydrobenzothiazole

[0018] Add 30g of the product from the previous step to 450ml of ethyl acetate, slowly add 55g of DBDMH at room temperature, finish adding in 2 hours, keep warm for 2 hours until the bromination reaction is complete as detected by TLC, gradually raise the temperature, control the temperature at 40-50°C, and put 35g of thiourea After the addition was complete, continue heating to reflux and...

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PUM

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Abstract

The invention discloses process for synthesizing an intermediate of (S)-2,6-diamino-4,5,6,7-tetralinbenzothiazole of an anti-parkinson drug. 4-acetamidocyclohexanol is used as a raw material, and a novel composite oxidant TEMPO / DBDMH is adopted. In the process, the novel composite oxidant TEMPO / DBDMH is adopted, reaction time is greatly shortened, reaction selectivity is good, a toxic reagent is prevented from being used, quality is good, operation is easy, and the process is environment-friendly. The process uses DBDMH (dibromohydantoin) to replace liquid bromine to conduct bromination, product positioning is good, and operation is safe.

Description

technical field [0001] The invention relates to the field of medicine synthesis technology, in particular to a synthesis technology of anti-Parkinson drug intermediate (S)-2,6-diamino-4,5,6,7-tetrahydrobenzothiazole. Background technique [0002] Anti-Parkinson pramipexole intermediate, namely (S)-2,6-diamino-4,5,6,7-tetrahydrobenzothiazole, introduced in CN1772744A, uses 4-aminocyclohexanol as raw material, through N - The acetylation reaction implements amino protection, and the Jones reagent is oxidized to obtain 4-acetylaminocyclohexanone. Then thiazole ring formation, HBr hydrolysis, tartaric acid chiral resolution five-step reaction to prepare. The operation is cumbersome, the reaction cycle is long, and highly corrosive raw materials such as Jones reagent, bromine, and HBr are used, which are harmful to the environment. The oxidation of secondary alcohols by TEMPO (tetramethylpiperidine oxide) has been proven to be an effective green process, but there is no report ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/82
Inventor 于振云付雪莲姚亚尊闫领旗于素云
Owner EASTSKY PHARM ANHUI TECH
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