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A kind of preparation method of 1-(3-chloropyrazolo[1,5a]-4,5,6,7-tetrahydropyridin-2-yl)-5-methanaminepyrazole-4-carbonitrile

A technology of tetrahydropyridine and carbonitrile, which is applied in the preparation of organic intermediates and 1--5-methylaminopyrazole-4-carbonitrile, can solve the problem of high production equipment and production conditions, increasing Problems such as purification process and separation difficulty, low material utilization rate, etc., to achieve low production cost, avoid separation and purification process, and high reaction efficiency

Active Publication Date: 2021-08-13
湖北相和精密化学有限公司
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Problems solved by technology

[0004] However, there are obvious defects and deficiencies in the above-mentioned prior art: one, the methylating reagent is methyl chloride, which is gaseous and expensive, and gaseous methyl chloride and liquid 1-(3-chloropyrazolo[1,5a] -4,5,6,7-tetrahydropyridin-2-yl)-5-aminopyrazole-4-carbonitrile solution reaction has the disadvantages of low reaction efficiency, low material utilization rate and high production cost; The reaction is a pressurized reaction, which requires high production equipment and production conditions, which increases the safety risk of production; the third is that the above-mentioned chemical reaction cannot avoid dimethylated by-products, that is, the reaction will generate 1-(3-chloropyrazolo [1,5a]-4,5,6,7-tetrahydropyridin-2-yl)-5-dimethylaminopyrazole-4-carbonitrile, reduces 1-(3-chloropyrazolo[1, 5a] The yield and purity of -4,5,6,7-tetrahydropyridin-2-yl)-5-methylaminopyrazole-4-carbonitrile also increase the subsequent purification process and separation difficulty

Method used

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  • A kind of preparation method of 1-(3-chloropyrazolo[1,5a]-4,5,6,7-tetrahydropyridin-2-yl)-5-methanaminepyrazole-4-carbonitrile
  • A kind of preparation method of 1-(3-chloropyrazolo[1,5a]-4,5,6,7-tetrahydropyridin-2-yl)-5-methanaminepyrazole-4-carbonitrile
  • A kind of preparation method of 1-(3-chloropyrazolo[1,5a]-4,5,6,7-tetrahydropyridin-2-yl)-5-methanaminepyrazole-4-carbonitrile

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Experimental program
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Effect test

Embodiment 1

[0040] 1) Etherification reaction: Add 1-(3-chloropyrazolo[1,5a]-4,5,6,7-tetrahydropyridin-2-yl)-5-aminopyrazole-4- 26.5g of formonitrile, 132g of ethylbenzene, 53g of trimethyl orthoformate and 0.22g of m-nitrobenzenesulfonic acid monohydrate, heated up to 70-80°C under stirring, and reacted for 20h under vacuum to 0.05Mpa to obtain a reaction solution A;

[0041] 2) Purification: Add 100ml of saturated aqueous sodium bicarbonate solution to the reaction solution A, stir for 10min, let it stand for 30min, separate the liquid and discard the water layer, add 10g of anhydrous magnesium sulfate to the organic layer, and filter after standing for 5h to obtain the filtrate A ;

[0042] 3) Rearrangement reaction: Add 1.1 g of tributylamine hydrochloride to filtrate A, react at 100-110°C for 12 hours, cool down to 40°C, and obtain reaction liquid B;

[0043] 4) Formylation reaction: first add 70ml of water to the reaction solution B, then add 15g of 98wt% sulfuric acid, react at 4...

Embodiment 2

[0046] 1) Etherification reaction: Add 1-(3-chloropyrazolo[1,5a]-4,5,6,7-tetrahydropyridin-2-yl)-5-aminopyrazole-4- 26.5g of formonitrile, 265g of xylene, 53g of trimethyl orthoformate and 0.68g of zinc chloride were heated to 90-100°C under stirring, and the reaction was carried out at a vacuum of 0.06Mpa for 10 hours to obtain reaction solution A;

[0047] 2) Purification: add 100 ml of water to the reaction solution A, stir for 10 minutes, let it stand for 30 minutes, separate the liquid and discard the water layer, add 10 g of anhydrous magnesium sulfate to the organic layer, and filter after standing for 5 hours to obtain the filtrate A;

[0048] 3) Rearrangement reaction: Add 3.2 g of tetrabutylammonium bromide to filtrate A, react at 130-140°C for 5 hours, cool down to 50°C, and obtain reaction liquid B;

[0049] 4) Formylation reaction: first add 70ml of water to the reaction solution B, then add 21g of 60wt% nitric acid, react at 50-60°C for 4h, and obtain the reactio...

Embodiment 3

[0052] 1) Etherification reaction: Add 1-(3-chloropyrazolo[1,5a]-4,5,6,7-tetrahydropyridin-2-yl)-5-aminopyrazole-4- 26.5g of formonitrile, 150g of chlorobenzene, 21.2g of trimethyl orthoformate and 0.6g of copper acetate monohydrate were heated to 80-90°C under stirring, and reacted for 15 hours under vacuum to 0.07Mpa to obtain reaction solution A;

[0053] 2) Purification: add 100 ml of water to the reaction solution A, stir for 10 minutes, let it stand for 30 minutes, separate the liquid and discard the water layer, add 10 g of anhydrous magnesium sulfate to the organic layer, let it stand for 8 hours, and then filter to obtain the filtrate A;

[0054] 3) Rearrangement reaction: Add 1.86 g of benzyltrimethylammonium chloride to the filtrate A, react at 120-130°C for 10 hours, cool down to 60°C, and obtain reaction solution B;

[0055] 4) Formylation reaction: firstly add 70ml of water to the reaction solution B, then add 20g of 98wt% sulfuric acid, react at 60-70°C for 8 ho...

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Abstract

The present invention relates to a kind of preparation of 1-(3-chloropyrazolo[1,5a]-4,5,6,7-tetrahydropyridine-2-yl)-5-methylamine pyrazole-4-carbonitrile Method, with 1-(3-chloropyrazolo[1,5a]-4,5,6,7-tetrahydropyridine-2-yl)-5-aminopyrazole-4-carbonitrile as starting material, After successively etherification reaction, purification, rearrangement reaction, deformylation reaction and filtration drying process. The preparation method of the present invention has high reaction efficiency, mild reaction conditions, improved production safety and equipment versatility, and the prepared finished product 1-(3-chloropyrazolo[1,5a]-4,5,6, 7-tetrahydropyridine-2-yl)-5-methylaminopyrazole-4-carbonitrile has the advantages of high yield, high purity and low production cost.

Description

technical field [0001] The invention relates to a preparation method of an organic intermediate, in particular to 1-(3-chloropyrazolo[1,5a]-4,5,6,7-tetrahydropyridin-2-yl)-5-methylamine The preparation method of pyrazole-4-carbonitrile belongs to the technical field of chemical industry. Background technique [0002] 1-(3-Chloropyrazolo[1,5a]-4,5,6,7-tetrahydropyridin-2-yl)-5-methylaminopyrazole-4-carbonitrile is the preparation The key intermediate, 1-(3-chloropyrazolo[1,5a]-4,5,6,7-tetrahydropyridin-2-yl)-5-methanaminepyrazole-4-carbonitrile is further processed by one step The chemical reaction can get dipacenil. At present, there are few literatures about 1-(3-chloropyrazolo[1,5a]-4,5,6,7-tetrahydropyridin-2-yl)-5-methylaminopyrazole-4-carbonitrile Preparation method. In 2012, Ge Faxiang disclosed a 1-(3-chloropyrazolo[1,5a]-4, The preparation method of 5,6,7-tetrahydropyridin-2-yl)-5-methylaminopyrazole-4-carbonitrile, that is, 1-(3-chloropyrazolo[1,5a]-4,5, 6,7-te...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
Inventor 易章国
Owner 湖北相和精密化学有限公司
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