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Preparation method of 2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole

A technology of benzothiazole and propylamino, applied in the field of medicine, can solve the problems of low reaction safety, unfavorable, difficult preparation, etc., and achieves the effects of simple raw materials, easy availability of raw materials, and improved reaction safety.

Inactive Publication Date: 2013-07-03
TIANJIN INSTITUTE OF PHARMA RESEARCH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The purpose of the present invention is to overcome the above-mentioned shortcoming that the above-mentioned method is difficult to obtain, low reaction safety is unfavorable for industrialized production, provides a kind of 2-amino-6-propylamino-4,5 that raw material is simple and easy to obtain, and reaction safety is high, 6, the preparation method of 7-tetrahydrobenzothiazole

Method used

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  • Preparation method of 2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole
  • Preparation method of 2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole

Examples

Experimental program
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Effect test

Embodiment 1

[0021] 0.18 M NaBH 4 Add it into a three-necked reaction flask containing 50 ml of anhydrous tetrahydrofuran, pass through nitrogen protection, and add 0.02 moles of 2-amino-6-propionylamino-4,5 under the condition of constant stirring at 0-5°C, 6,7-Tetrahydrobenzothiazole, after mixing evenly, slowly drop into 100 ml of 0.08 mole I 2 THF solution (0.08 mol I 2 ), the time is 3-4 hours. Then, the temperature was controlled at 0-5° C. and the reaction was continuously stirred for 10 hours, and the reaction mixture was heated to 50° C. for 12 hours. Then cool under an ice bath.

[0022] Add 350 milliliters of 10% hydrochloric acid solution to the above-mentioned reacted mixture, adjust the pH value to 9-10 with 20% NaOH solution, extract in portions with ethyl acetate, add anhydrous sodium sulfate to the extract to dry, The solvent was evaporated to obtain a solid product, which was dried in vacuo to obtain 2.54 g of 2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole, and...

Embodiment 2

[0025] 0.18 M NaBH 4 Add it into a three-necked reaction flask containing 50 ml of anhydrous tetrahydrofuran, pass through nitrogen protection, and add 0.02 moles of 2-amino-6-propionylamino-4,5 under the condition of constant stirring at 0-5°C, 6,7-Tetrahydrobenzothiazole, after mixing evenly, slowly drop into 100 milliliters of 0.08 moles of I 2 Tetrahydrofuran, ether solution (0.08 moles I 2 , the volume ratio of tetrahydrofuran to diethyl ether is 1:1), reacted at 0-5°C for 12 hours under constant stirring, then heated the reaction mixture to 35°C for 12 hours, and then cooled it in an ice bath.

[0026] Add 360 milliliters of 10% hydrochloric acid solution to the above-mentioned reacted mixture, adjust the pH value to 9-10 with 20% NaOH solution, extract in portions with ethyl acetate, add anhydrous sodium sulfate to the extract to dry, The solvent was evaporated to obtain a solid product, which was dried in vacuo to obtain 2.75 g of 2-amino-6-propylamino-4,5,6,7-tetrah...

Embodiment 3

[0029] 0.04 M NaBH 4 Add it into a three-necked reaction flask containing 50 ml of anhydrous tetrahydrofuran, pass through nitrogen protection, and add 0.02 moles of 2-amino-6-propionylamino-4,5 under the condition of constant stirring at 0-5°C, 6,7-Tetrahydrobenzothiazole, after mixing evenly, slowly drop into 100 milliliters of 0.16 moles of I 2 Tetrahydrofuran, ether solution (0.16 moles I 2 , the volume ratio of tetrahydrofuran to diethyl ether is 1:4), reacted at 0-5°C for 12 hours under constant stirring, then heated the reaction mixture to 40°C for 20 hours, and then cooled it in an ice bath.

[0030] Add 360 milliliters of 10% hydrochloric acid solution to the above-mentioned reacted mixture, adjust the pH value to 9-10 with 20% NaOH solution, extract in portions with ethyl acetate, add anhydrous sodium sulfate to the extract to dry, The solvent was evaporated to obtain a solid product, which was dried in vacuo to obtain 2.33 g of 2-amino-6-propylamino-4,5,6,7-tetrah...

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Abstract

The invention provides a preparation method of 2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole. According to the preparation method, 2-amino-6- propionamido-4,5,6,7-tetrahydrobenzothiazole is adopted as a raw material and is reduced through I2 and sodium borohydride to prepare the 2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole. The preparation method has the advantages that the raw material is easy to obtain, the reaction condition is mild, the control is easy and the reaction safety is high; and the preparation method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a preparation method of 2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole. Background technique [0002] 2-Amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole, the structural formula is as follows: [0003] [0004] The mixture can be resolved to obtain the product (S)-(-)2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole, and its dihydrochloride is pramipexole hydrochloride, Wherein (S) means S configuration, (-) means left-handed. Pramipexole hydrochloride can be used as a pharmaceutical raw material for the treatment of Parkinson's disease. Pramipexole hydrochloride must be in S configuration and L-rotational to have a medical effect. The method for preparing (S)-(-)2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole in the synthetic pramipexole hydrochloride mainly contains at present: [0005] J.Med.chem.1987,30,494-498 discloses a kind of prepara...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/82
Inventor 王浩李泽晨史可吟靳朝东
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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