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Preparation method of Trelagliptin

A single and mixed solvent technology, applied in organic chemistry and other fields, can solve the problems of increased impurities, many side reactions, and high cost

Inactive Publication Date: 2016-06-01
SHANGHAI YUANZHI BIOMEDICAL SCI & TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Sealing reaction is a high-temperature and high-pressure reaction, which is very dangerous to scale up, poor in operability, high in equipment requirements, and high in cost
In addition, under high temperature and high pressure conditions, there are many side reactions and impurities increase
And the post-treatment of this method needs to use column chromatography or HPLC to separate, and the cost is very high, is unfavorable for large-scale production

Method used

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  • Preparation method of Trelagliptin
  • Preparation method of Trelagliptin
  • Preparation method of Trelagliptin

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0025] Add 2-(6-chloro-3-methyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-methyl)-4-fluorobenzonitrile (2.930g, 0.010mol), dioxane (20ml), (R)-3-aminopiperidine bishydrochloride (2.070g, 0.012mol) and sodium bicarbonate (2.5g, 0.03mol) were added under stirring. The reaction was stirred at 75 degrees Celsius for 5 hours. LC-Ms detected that the reaction was complete and concentrated under reduced pressure. The crude product was refluxed with 20ml ethyl acetate for 1 hour, filtered while hot, and the filtrate was allowed to stand overnight. A solid precipitated out. The product was collected by filtration.

example 2

[0027] Add 2-(6-chloro-3-methyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-methyl)-4-fluorobenzonitrile (29.3g, 0.1mol), dioxane (200ml), (R)-3-aminopiperidine bishydrochloride (20.7g, 0.12mol) and triethylamine (30.3g, 0.3mol) were added under stirring. The reaction was stirred at 70 degrees Celsius for 3 hours. LC-Ms detected that the reaction was complete. The reaction solution was cooled to room temperature, poured into 500 ml ice water, stirred at 5-10 degrees Celsius for 2 hours, filtered, and the solid was collected to obtain the product.

example 3

[0029] Add 2-(6-chloro-3-methyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-methyl)-4-fluorobenzonitrile (2.930g, 0.010mol), acetonitrile (15ml), (R)-3-aminopiperidine bishydrochloride (2.07g, 0.012mol) and potassium carbonate (4.14g, 0.03mol) were added with stirring. The reaction was stirred at 75 degrees Celsius for 5 hours. LC-Ms detected that the reaction was complete. The reaction solution was cooled to room temperature, poured into 50 ml ice water, stirred at 5-10 degrees Celsius for 2 hours, filtered, and the solid was collected to obtain the product.

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Abstract

The invention belongs to the technical field of medicinal chemistry and particularly relates to a preparation method of Trelagliptin. The equation is shown in the specification. In the method, 2-(6-chloro-3-methyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-methyl)-4-fluorobenzonitrile and (R)-3-aminopiperidine dihydrochloride are subjected to a normal-pressure reaction in a single organic solvent or a mixed solvent under the alkaline condition of an acid-binding agent, and then a Trelagliptin compound is obtained. By means of the method, a high-pressure reaction is avoided, and thus reaction safety is greatly enhanced. The reaction condition of the method is mild and easy to control, and the method can be applied to industrial production and preparation of Trelagliptin.

Description

Technical field [0001] The invention belongs to the technical field of medicinal chemistry, and specifically relates to a preparation method of troxagliptin. Background technique [0002] The 2011 report of the World Health Organization pointed out that there are about 350 million people living with diabetes in the world. According to reports, there are more than 100 million people with diabetes in China. [0003] Diabetes is a chronic metabolic disease. If it is not well controlled, it is prone to complications such as diabetic nephropathy, neuropathy and vascular disease. Diabetes patients generally need to take long-term medications. Long-acting diabetes medications have obvious advantages in patient compliance and other aspects, and are a trend in diabetes medications. At present, the marketed diabetes drugs that can be administered weekly are mainly biological drugs such as GLP-1 analog Exenatide long-acting preparations and Albiglutide, which require injections. [0004] DPP-...

Claims

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Application Information

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IPC IPC(8): C07D401/04
CPCC07D401/04
Inventor 栾德刚秦立玙栾松平
Owner SHANGHAI YUANZHI BIOMEDICAL SCI & TECH CO LTD
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