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Vilazodone intermediate synthesis method

A synthesis method and vilazodone technology are applied in the field of synthesizing vilazodone intermediates, and can solve the problems of low yield, cumbersome post-processing, long reaction time and the like, so as to shorten the reaction time, simplify the production process, The effect of improving product yield

Active Publication Date: 2018-01-05
连云港恒运药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the cyclization process, there are problems such as long reaction time, low yield and cumbersome post-treatment, so it is necessary to seek a synthetic method with easier operation and higher yield

Method used

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  • Vilazodone intermediate synthesis method

Examples

Experimental program
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Effect test

Embodiment 1

[0030]

[0031] Add 19.1 g of 6-nitrocoumarin, 8.3 g of sodium hydroxide, 100 ml of ethanol, and 100 ml of water into the reaction flask, and heat to reflux for 4 hours. After the reaction was completed, dilute hydrochloric acid was added to adjust the pH to 3-4, filtered, and vacuum-dried to obtain 17.6 g of 3-(2-hydroxy-5-nitrophenyl)acrylic acid, with a yield of 84.1%.

Embodiment 2

[0033]

[0034] Dissolve 20.9 g of 3-(2-hydroxy-5-nitrophenyl)acrylic acid prepared in Example 1 in 100 ml of DMF, add 2.1 g of copper chloride and 5.0 g of cesium carbonate, and heat to 100°C for 5 hours to react. After completion, the reaction solution was poured into 300ml of ice water, filtered, and the filter cake was vacuum-dried and recrystallized with 250ml of ethanol / water mixed solvent to obtain 17.6g of 5-nitrobenzofuran-2-carboxylic acid, with a yield of 85.0%, a purity of 97.7%.

Embodiment 3

[0036]

[0037] Dissolve 20.9 g of 3-(2-hydroxy-5-nitrophenyl)acrylic acid prepared in Example 1 in 100 ml of DMSO, add 2.5 g of cuprous iodide and 5.0 g of cesium carbonate, and heat to 100° C. for 5 hours. After the reaction was completed, the reaction solution was poured into 300 ml of ice water, filtered, and the filter cake was vacuum-dried and recrystallized with 250 ml of ethanol / water mixed solvent to obtain 15.9 g of 5-nitrobenzofuran-2-carboxylic acid, with a yield of 76.7%. Purity 95.0%.

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Abstract

The invention discloses a Vilazodone intermediate synthesis method. According to the Vilazodone intermediate synthesis method, 6-nitrocoumarin serves as an initial raw material, through the steps of ring opening, intramolecular cyclization, esterification, reduction, piperazine-ring preparation and the like, the key Vilazodone intermediate 5-(1-piperazinyl)-2-benzofuran-2-carboxylic acid ethyl ester shown in the formula I is obtained. The Vilazodone intermediate synthesis method is simple is synthesis path, the yield of the targeted product is high, and the Vilazodone intermediate synthesis method is suitable for industrial large-scale production.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a method for synthesizing a vilazodone intermediate. Background technique [0002] Vilazodone hydrochloride (Vilazodone hydrochloride), the chemical name is 5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-2-benzene Furamide hydrochloride is a new antidepressant drug developed by Clinical Data. In January 2011, the U.S. Food and Drug Administration (FDA) approved vilazodone hydrochloride tablets for the treatment of moderate to severe depressive disorder (MDD) in adults. Compared with existing clinical antidepressants, vilazodone hydrochloride has a rapid onset of action. , high safety, and no side effects of sexual dysfunction for patients. Its chemical structure is as shown in formula (A): [0003] [0004] 5-(1-piperazinyl)-2-benzofuran carboxylic acid ethyl ester is an important intermediate in the synthesis of vilazodone hydrochloride, and the route of vilazodone hydr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/85
Inventor 董淑求冯芮茂张庆捷
Owner 连云港恒运药业有限公司
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