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A kind of preparation method of N-(aminothiomethyl)-5-oxo-1-propyl-2-pyrrolidineacetamide

A technology of aminothiomethyl and pyrrolidine acetamide, which is applied in the field of preparation of N--5-oxo-1-propyl-2-pyrrolidine acetamide, and can solve the problems such as the synthesis report of no impurities found

Active Publication Date: 2015-08-26
CHINA RESOURCES SAIKE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

2. Strong safety: As a non-ergot drug, Senfulo has no clear adverse reaction of ergot agonist-related heart valve disease
Unfortunately, through literature search, we did not find any synthesis reports about this impurity

Method used

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  • A kind of preparation method of N-(aminothiomethyl)-5-oxo-1-propyl-2-pyrrolidineacetamide
  • A kind of preparation method of N-(aminothiomethyl)-5-oxo-1-propyl-2-pyrrolidineacetamide
  • A kind of preparation method of N-(aminothiomethyl)-5-oxo-1-propyl-2-pyrrolidineacetamide

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Experimental program
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Embodiment 1

[0020] Embodiment one: the preparation of BI-II751XX

[0021] 1. Synthesis of 5-(p-toluenesulfonylmethyl)-2-pyrrolidone (751M-01)

[0022] Dissolve 45g of pyroglutaminol in 600ml of dichloromethane, add 7.2g of DMAP and 60ml of triethylamine, stir at room temperature for 15min, add 82.2g of p-toluenesulfonyl chloride in batches, exotherm during the addition, and stir at room temperature for 14h , TLC to monitor the reaction (ethyl acetate: ethanol = 4:1, iodine smoked), after the reaction of the raw materials is complete, add 400ml of dichloromethane, then add 200ml of 1N hydrochloric acid solution, stir for 20min, separate the liquid, and separate the organic layer Wash with 400ml of water and 400ml of saturated brine, add 100g of anhydrous sodium sulfate to dry, filter, and evaporate the filtrate to dryness to obtain 102g of the product, with a yield of 97.14%.

[0023] 2. Synthesis of 5-(cyanomethyl)-2-pyrrolidone (751M-02)

[0024] Dissolve 49.3g of 5-(p-toluenesulfonylm...

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Abstract

The invention discloses a preparation method of N-(amino sulfo methyl)-5-oxo-1-propyl-2-pyrrolidine acetamide; the method adopts pyroglutaminol as an initial material, and allows pyroglutaminol to react with p-toluene sulfonyl chloride to generate active ester; then cyanidation with potassium cyanide, N-alkylation with bromopropane, alcoholysis, and hydrolysis are performed to obtain 5-(carboxymethyl)-N-propyl-2-pyrrolidone; and reaction with thiourea is performed to obtain N-(amino sulfo methyl)-5-oxo-1-propyl-2-pyrrolidine acetamide. The beneficial effect of the invention is that the invention prepares a standard substance of impurity BI-II751XX with purity more than 98%.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry and relates to a preparation method of N-(aminothiomethyl)-5-oxo-1-propyl-2-pyrrolidineacetamide. Background technique [0002] Senfulol (pramipexole) is currently the first-line treatment drug recommended by the American Academy of Neurology, the Movement Disorder Society, and the treatment guidelines for Parkinson's disease in various countries. Senfulol (pramipexole hydrochloride tablets) is a new generation of non-ergot dopamine receptor agonists, the main component of the drug is (S)-2-amino-4,5,6,7-tetrahydrochloride monohydrate -6-Propylamine-benzothiazole (pramipexole hydrochloride monohydrate). Senfulol is mainly used to treat the signs and symptoms of idiopathic Parkinson's disease. This drug can be used alone or in combination with levodopa preparations (such as Sining and Madopar). Especially in the late stage of the disease, when the effect of levodopa gradually weakens or changes...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/26
Inventor 贾贵鹏李志强李继斌邹江杨琰
Owner CHINA RESOURCES SAIKE PHARMA