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Method for synthesizing trazodone

A synthetic method, letrozole technology, applied in the field of drug synthesis, can solve the problems of difficult removal of impurities, low purity, low yield of letrozole, etc., and achieve the effect of being suitable for large-scale production and mild reaction conditions

Active Publication Date: 2013-04-10
BENGBU BBCA MEDICINE SCI DEV
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  • Abstract
  • Description
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AI Technical Summary

Problems solved by technology

The yield of letrozole obtained in the second step reaction is low and the purity is not high, and impurities are difficult to remove

Method used

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  • Method for synthesizing trazodone
  • Method for synthesizing trazodone

Examples

Experimental program
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Effect test

Embodiment 1

[0025] Add 500mL tetrahydrofuran dried over anhydrous magnesium sulfate into a 2000mL reaction bottle, add 36g sodium methoxide under nitrogen protection under stirring, cool down to below 0°C in an ice-salt bath, slowly add 117g p-toluonitrile and 125g p-fluorobenzonitrile tetrahydrofuran dropwise Mix the solution and keep it below 0°C for 2 hours after dropping. Wash 3 times with 300 mL of saturated brine, dry over anhydrous sodium sulfate, distill THF off, and crystallize the residue with methyl tert-butyl ether to obtain 113 g of Intermediate I, melting point: 168.5°C, HPLC purity: 99.7%

[0026] 113g of intermediate I obtained above was dissolved in 600mL of chloroform, 92g of N-bromosuccinimide and 4g of azobisisobutyronitrile were added in sequence, the mixture was heated to reflux temperature and kept at this temperature for 9-10h. The reaction solution was cooled to room temperature, and the chloroform layer was washed three times with 300 mL of saturated saline, drie...

Embodiment 2

[0029] Synthesis of 4,4'-cyanodiphenylmethane

[0030] Add 500mL of tetrahydrofuran dried over anhydrous magnesium sulfate into a 2000mL reaction bottle, add 32.5g of sodium methoxide under stirring and nitrogen protection, cool down to below 5°C in an ice-salt bath, slowly add 117g of p-toluonitrile and 133g of p-fluorobenzonitrile dropwise The mixed solution of tetrahydrofuran was kept below 0°C for 2 hours after dropping. Wash 3 times with 300 mL of saturated brine, dry over anhydrous sodium sulfate, evaporate THF, and crystallize the residue with methyl tert-butyl ether to obtain 109 g of intermediate I, melting point: 168.9 °C, HPLC purity: 98.2%

[0031] Synthesis of 4-(α-bromo-4-cyano)benzonitrile

[0032] 113g of intermediate I was dissolved in 600mL of chloroform, 100g of N-bromosuccinimide and 2g of azobisisobutyronitrile were added in sequence, the mixture was heated to reflux temperature and kept at this temperature for 9-10h. The reaction solution was cooled to ...

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Abstract

The invention discloses a method for synthesizing trazodone, which comprises the following steps: 1. firstly synthesizing a midbody I of 4, 4'-cyano-diphenyl methane; 2. then, using catalysts to enable the midbody I to take bromination reaction for obtaining a midbody II of 4-(alpha-bromo-4-cyano) cyanobenzene; and 3 finally carrying out condensation on the midbody II and 1, 2, 4-triazole to generate letrozole crude products, and carrying out recrystallization. When the method is used, high-purity products can be easily obtained, the reaction conditions are mild and economic, and the method is applicable to large-scale production.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a method for synthesizing letrozole. Background technique [0002] Letrozole (Letrozole) is a third-generation aromatase inhibitor developed by Novartis Co., Ltd. in Switzerland. It is a synthetic benzyltriazole derivative and was first launched in the UK in 1996. Letrozole reduces the level of estrogen by inhibiting aromatase, thereby eliminating the stimulating effect of estrogen on tumor growth. In vivo and in vitro studies have shown that letrozole can effectively inhibit the transformation of androgen into estrogen, and estrogen in postmenopausal women mainly comes from the aromatization of androgen precursors in peripheral tissues, so it is especially suitable for postmenopausal breast cancer patient. The in vivo activity of letrozole is 150-250 times stronger than that of the first-generation aromatase inhibitor aminoglutethimide. Because of its high selectivity, it does n...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/08
Inventor 李立标陈文婕孙建华韦亚峰
Owner BENGBU BBCA MEDICINE SCI DEV
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