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Method for preparing amrinone midbody

An intermediate, amrinone technology, applied in the field of pharmaceutical chemical synthesis, can solve the problems of many impurities, easy agglomeration, unstable product quality, etc., and achieve the effect of high quality and high yield

Inactive Publication Date: 2015-04-29
丹阳恒安化学科技研究所有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Chinese patent 200610165391.8 introduces a preparation method of amrinone intermediate, which reacts 4-picoline and N,N-dimethylformamide in the presence of phosphorus oxychloride to generate an intermediate compound, and then reacts with cyanoacetoacetate Amide reaction, the target product is obtained after separation, this preparation method uses DMF as the solvent, the yield is about 70%, and the quality of the prepared product is unstable, with many impurities and easy to agglomerate

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  • Method for preparing amrinone midbody

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Experimental program
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Effect test

Embodiment 1

[0012] Add 500ml of tetrahydrofuran to the three-necked flask, control the reaction temperature at 10-20°C, add 400g of phosphorus oxychloride dropwise, and then add 74g of 4-picoline dropwise. Add the reaction solution dropwise to 2-3L of water, and adjust the pH value within the range of 8-9 with 40wt% sodium hydroxide solution; cool and filter with suction to obtain a brown-yellow filtrate, heat it to 10-20°C, and add 125g For cyanoacetamide, add 40wt% sodium hydroxide solution dropwise to adjust the pH value to the range of 9-10, control the temperature and react at no more than 20°C for 2-3h to obtain 148.9g of yellow solid, add water and heat to 50-70°C to dissolve , add 1g of activated carbon and 3g of sodium metabisulfite, adjust the pH value to 5-6 with acetic acid, cool, filter with suction, and dry to obtain 133.4g of a yellow solid with a yield of 78%.

Embodiment 2

[0014] Add 500ml of tetrahydrofuran to the three-necked flask, control the reaction temperature at 10-20°C, add 400g of phosphorus oxychloride dropwise, then add 55g of 4-picoline dropwise, and react for 2-3h after the dropwise addition, and put it under ice bath Add the reaction solution dropwise to 2-3L of water, and adjust the pH value within the range of 8-9 with 40wt% sodium hydroxide solution; cool and filter with suction to obtain a brown-yellow filtrate, heat it to 10-20°C, and add 105g For cyanoacetamide, add 40wt% sodium hydroxide solution dropwise to adjust the pH value to the range of 9-10, control the temperature and react at no more than 20°C for 2-3h to obtain 128.6g of yellow solid, add water and heat to 50-70°C to dissolve , adding 1g of activated carbon and 1.3g of sodium metabisulfite, adjusting the pH value to 5-6 with acetic acid, cooling, suction filtration, and drying to obtain 105.5g of a yellow solid with a yield of 75%.

Embodiment 3

[0016] Add 500ml of tetrahydrofuran to the three-necked flask, control the reaction temperature at 10-20°C, add 400g of phosphorus oxychloride dropwise, and then add 63g of 4-picoline dropwise. Add the reaction solution dropwise to 2-3L of water, and adjust the pH value within the range of 8-9 with 40wt% sodium hydroxide solution; cool and filter with suction to obtain a brown-yellow filtrate, heat it to 10-20°C, and add 113g For cyanoacetamide, add 40wt% sodium hydroxide solution dropwise to adjust the pH value to the range of 9-10, control the temperature and react at no more than 20°C for 2-3h to obtain 135.7g of yellow solid, add water and heat to 50-70°C to dissolve , adding 1g of activated carbon and 2g of sodium metabisulfite, adjusting the pH value to 5-6 with acetic acid, cooling, suction filtration, and drying to obtain 119.8g of a yellow solid with a yield of 77%.

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Abstract

The invention discloses a method for preparing an amrinone midbody. The method comprises the following steps: at the temperature of 10-20 DEG C, under the condition that phosphorus oxychloride and tetrahydrofuran exist, enabling 4-methylpyridine and N,N-dimethyl formamide to react to generate an intermediate state compound, performing reaction on the intermediate state compound and cyanoacetamide to obtain a crude product, and treating the crude product by active carbon and sodium pyrosulfite to obtain a target product. Compared with the prior art, the method for preparing the amrinone midbody has the advantages that tetrahydrofuran replaces DMF and serves as a solvent, so that the yield is increased; sodium pyrosulfite is used as an antioxidant for the crude product, so that the prepared quality product is high in quality, high in stability and unlikely to cake.

Description

technical field [0001] The present invention relates to a preparation method of a cardiotonic intermediate, in particular to a compound 5-cyano-(3,4 ' The invention discloses a preparation method of -bipyridine)-6(H)-ketone, which belongs to the field of pharmaceutical chemical synthesis. Background technique [0002] Amrinone, also known as Amrinone, Amrinone, Amrinone, Amrinone, Ampirone, Anlianone, Anoke, Qiangxinlong, Amrinone Lactate, is a new type of non-glucoside, non- Catecholamine cardiotonic drugs, both oral and intravenous injection are effective, have both positive inotropic effect and vasodilation effect, can increase myocardial contractility, increase cardiac blood volume, reduce cardiac preload and afterload, and reduce left ventricular filling pressure. Improve left ventricular function, increase cardiac index, but have no significant effect on mean arterial pressure and heart rate, and do not cause arrhythmia. It can still enhance atrioventricular node fun...

Claims

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Application Information

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IPC IPC(8): C07D213/85
CPCC07D213/85
Inventor 陈国平夏方方杜成铭陈丽庆王霞张梁吴涛英荆吉仁夏新开王海大
Owner 丹阳恒安化学科技研究所有限公司