Method for synthesizing Vardenafil hydrochloric acid

A technique of vardenafil hydrochloride and a synthetic method, which is applied in the field of organic synthesis, can solve the problems affecting the state and purity of product VI, reduce the yield of product VII, and the product is not easy to precipitate, so as to achieve easy operation, reduce production cost, and react easy effect

Inactive Publication Date: 2007-10-10
BEIJING UNIV OF CHEM TECH
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

[0012] (1) in reaction [A], because raw material II activity is too strong, easily decomposes in simple sodium hydroxide solution, thereby reduces the yield of product I;
[0013] (2) In the reaction [F], the intermediate product is not post-treated, and the one-pot method is used to complete the two-step ring formation, and the yield is low; in additio

Method used

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  • Method for synthesizing Vardenafil hydrochloric acid
  • Method for synthesizing Vardenafil hydrochloric acid
  • Method for synthesizing Vardenafil hydrochloric acid

Examples

Experimental program
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Embodiment 1

[0045](1) Add 10.04g of D, L-alanine to a mixed solvent made of 56ml of acetone and 92ml of water, then add 6.24g of sodium hydroxide, then add dropwise 18ml of 9mol / L sodium hydroxide solution and 13ml of For n-butyryl chloride, maintain the reaction at 0-8°C for 1.5 hours, adjust the reaction solution to pH=1 with hydrochloric acid, extract with ethyl acetate, dry over anhydrous sodium sulfate, and distill under reduced pressure to obtain 2-butyrylaminopropionic acid (product 1 ) 13.66g, its yield is 76.2%.

[0046] (2) Dissolve 2.0 g of the product obtained in step (1) in 13 ml of tetrahydrofuran, add 0.06 g of 4-N, N lutidine, then add 3.2 g of pyridine, stir, and slowly add oxalyl chloride mono Ethyl ester was refluxed in an oil bath for 3 hours, filtered, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, and distilled under reduced pressure to obtain 3-butyrylamino-2-oxo-butyric acid ethyl ester (product 2) 1.90 g, the yield...

Embodiment 2

[0053] In step (1), the mixed solvent is 56ml of acetone and 56ml of water, and the weight of the obtained product 1 is 12.37g, and its yield is 69%. Other steps are with embodiment 1.

Embodiment 3

[0055] In step (1), the reaction solution was adjusted to pH=3 with hydrochloric acid, and the weight of product 1 was 11.86 g, and the yield was 66.2%. Other steps are with embodiment 1.

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Abstract

This invention relates to a method for synthesizing vardenafil hydrochloride. The method comprises: (1) performing acylation and nucleophilic addition on D,L-alanine raw material, condensing with 2-ethoxybenzamidine hydrochloride twice, and performing ring-closing reaction to obtain 2-(2-ethoxyphenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]-trizin-4-one; (2) performing sulfonation reaction to obtain 4-ethoxy-3-(3,4-dihydroxy-5-methyl-4-oxo-7-propyl imidazo[1,5-f][1,2,4]trizin-4-one)benzenesulfonic acid; (3) reacting with N-ethyl pyrazine to obtain vardenafil, and reacting with HCl to obtain vardenafil hydrochloride. The method has such advantages as easy operation, high yield, and simple process and low reaction condition requirement, thus is suitable for industrialization.

Description

technical field [0001] The invention relates to an organic synthesis method, in particular to a synthesis method of vardenafil hydrochloride. technical background [0002] The chemical name of vardenafil hydrochloride is: 2-[2-ethoxy-5-(4-ethylpiperazine-1-sulfonyl)phenyl]-5-methyl-7-propyl-3H- Imidazol[5,1-f][1,2,4]triazine-4-one monohydrochloride, English name: 2-[2-Ethoxy-5-(4-hydroxyethylpiperazine-1-sulphonyl)-phenyl ]-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]trizin-4-one hydroxhloride trihydrate, its structural formula is: [0003] [0004] Vardenafil hydrochloride (Vardenafil hydrochloride) is a kind of highly selective phosphodiesterase V (PDE5) inhibitor newly developed by German Bayer company in 2001, is a safe, Effective oral medication. [0005] Vardenafil hydrochloride is a PDE5 inhibitor drug. Its mechanism of action is: PDE5 is the main cGMP hydrolase in the corpus cavernosum of the human penis. When NO is released during sexual stimulation, it activate...

Claims

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Application Information

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IPC IPC(8): C07D487/04
Inventor 乔仁忠王辉郭亮
Owner BEIJING UNIV OF CHEM TECH
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