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Preparation method of urapidil

A technology of uradil and dimethyluracil, which is applied in the field of preparation of uradil, can solve the problems of expensive foreign products, no scale-up production, high cost, etc.

Pending Publication Date: 2022-02-18
苏州中科新药篮生物医药科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The raw materials used in this route are not produced domestically, and foreign products are expensive
[0007] In 2014, the patent CN104262264B, which was applied and authorized by Hebei Yipin Pharmaceutical Co., Ltd., chose route 1. This patent chose Pd / NHC as the catalytic system when synthesizing urapidil. Although the preparation process has the advantages of good selectivity and high yield, But this route needs to use Pd catalyst, the cost is high
This route has many side reactions and is difficult to post-process, so it is only suitable for small-scale reactions in the laboratory, and has no meaning for scale-up production.

Method used

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  • Preparation method of urapidil
  • Preparation method of urapidil
  • Preparation method of urapidil

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Embodiment 1

[0044] The present embodiment provides a kind of preparation method of urapidil, specifically comprises the following steps:

[0045] Step 1, the synthesis of 6-(3-hydroxypropylamino)-1,3-dimethyluracil

[0046] In a 500ml three-necked flask, add 3-amino-1-propanol (36.3g, 483.9mmol), add ammonium chloride (8.6g, 161.3mmol) and 1,3-dimethyl-6-amino Uracil (25.0g, 161.3mmol), heated to 100°C and stirred for 30min, then heated to 150°C, stirred for 2.5h to dissolve the system, and continued to maintain the temperature for 3h, TLC showed that the reaction was complete. Cool to 80°C and add 75ml of ethanol, the system dissolves, then slowly cool down to 10°C, a large amount of white solids precipitate out. Filtration, the filter cake was washed twice with acetone (2*100ml), and the product was dried at room temperature to obtain 6-(3-hydroxypropylamino)-1,3-dimethyluracil (24.1g white solid, yield 70.2% ), HPLC purity 97.1%.

[0047] LC-MS: m / z=214.1 [M+H] +

[0048] 1H NMR (...

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Abstract

The invention provides a preparation method of urapidil. The preparation method comprises the following steps: mixing 1, 3-dimethyl-6-aminouracil with 3-amino-1-propanol, and carrying out a reaction so as to prepare 6-(3-hydroxypropylamino)-1, 3-dimethyluracil; mixing 6-(3-hydroxypropylamino)-1, 3-dimethyluracil and thionyl chloride to react so as to prepare 6-(3-chloropropylamino)-1, 3-dimethyluracil; and enabling 6-(3-chloropropyl amino)-1, 3-dimethyluracil to react with 1-(2-methoxyphenyl) piperazine hydrochloride so as to obtain the urapidil. The preparation method has the advantages of simple operation, cheap and easily available reagents, few side reactions, high yield, good purity of the obtained product, and facilitation of industrial production.

Description

technical field [0001] The invention relates to a preparation method of urapidil, which belongs to the technical field of chemical synthesis. Background technique [0002] Urapidil is a selective α1-receptor blocker with dual peripheral and central hypotensive effects. Peripheral dilation of blood vessels is mainly through blocking post-synaptic α1 receptors, so that the peripheral resistance is significantly reduced and blood vessels are dilated. The central effect is to reduce blood pressure by activating 5-hydroxytryptamine-1A receptors and reducing the sympathetic feedback of the medullary cardiovascular regulation center. This product has the effect of blocking post-synaptic α1 receptors and blocking peripheral α2 receptors, but the former is the main one. The relaxation effect of this product on venous blood vessels is greater than that on arterial blood vessels, and can reduce renal vascular resistance. It has no antihypertensive effect on patients with normal blood...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/545
CPCC07D239/545
Inventor 邹晓丽唐朝徐旭纪宏宇周兴
Owner 苏州中科新药篮生物医药科技有限公司
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