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Acyl triazole compound as well as preparation method and application thereof

A technology of acyl triazoles and compounds, which is applied in the field of preparation of intermediate compounds of pomacoxib and its preparation, and can solve the problems of only 33% yield, difficult waste water treatment, poor effect, etc.

Active Publication Date: 2017-06-20
NINGBO BESTDRUG PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] There are two disadvantages in this reaction: (1) the by-product is cyanide, which is highly toxic and the wastewater is difficult to treat; (2) compound 04 will release highly toxic hydrocyanic acid after absorbing moisture
[0011] It has also been reported that 2-bromoisobutyryl bromide (compound 05) was used as a cyclizing agent (Bioorg.Med.Chem.2002, 10:1137-42), but the effect is not good, and the yield is only 33%

Method used

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  • Acyl triazole compound as well as preparation method and application thereof
  • Acyl triazole compound as well as preparation method and application thereof
  • Acyl triazole compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] Example 1: Preparation of 1-(2-bromoisobutyryl)-1,2,4-triazole

[0069] Mix 1.38g (20mmol) of 1,2,4-triazole with 13.9ml of tetrahydrofuran, stir, add dropwise 2.29g (10mmol) of pure 2-bromoisobutyryl bromide, drop it in about 30 minutes, and continue stirring for 2 hours. Filter to remove insoluble matter, and the filtrate is concentrated to dryness under reduced pressure. Add 5 ml of methyl tert-butyl ether, stir for 30 minutes, filter, and dry the filter cake to obtain 2.05 g of the product, with a yield of 94%.

[0070] 1 H-NMR (CDCl 3 , 400MHz): δ2.18(S,6H), 8.07(S,1H), 8.97(S,1H)

Embodiment 2

[0071] Example 2: Preparation of 1-(2-chloroisobutyryl)-1,2,4-triazole

[0072] Mix 1.64g (10mmol) of N,N'-carbonylbis(1,2,4-triazole) with 16.4ml of tetrahydrofuran, add 1.23g (10mmol) of 2-chloroisobutyric acid, and stir the reaction at 50°C for 2 hours. Cool and concentrate to dryness under reduced pressure. Add 10 ml of methyl tert-butyl ether, stir for 30 minutes, filter, and dry the filter cake to obtain 1.55 g of the product, with a yield of 89.3%.

[0073] 1 H-NMR (CDCl 3 , 400MHz): δ1.97(S,6H), δ7.93(S,1H), δ8.84(S,1H)

Embodiment 3

[0074] Example 3: Preparation of 1-(2-bromoisobutyryl)-3-methyl-1,2,4-triazole

[0075] Mix 1.66g (20mmol) of 3-methyl-1,2,4-triazole with 16.6ml of tetrahydrofuran, stir, add dropwise 2.29g (10mmol) of pure 2-bromoisobutyryl bromide, and drop it in about 30 minutes. Stirring was continued for 2 hours, filtered to remove insoluble matter, and the filtrate was concentrated to dryness under reduced pressure. Add 5 ml of methyl tert-butyl ether, stir for 30 minutes, filter, and dry the filter cake to obtain 2.09 g of the product, with a yield of 90%.

[0076] 1 H-NMR (CDCl 3 , 400MHz): δ2.17(S,6H), δ2.32(S,3H), δ8.77(S,1H)

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Abstract

The invention discloses an acyl triazole compound as well as a preparation method and an application thereof. The structural formula of the acyl triazole compound is as shown in a formula (I) in the specification, wherein in the formula (I), X is Cl, Br, I or OSO2R3; R3 is C1-C4 alkyl, phenyl or substituted phenyl; R1 and R2 are respectively independently H, halogens, CN, NO2, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkyl thio or NR4R5; and R4 and R5 are respectively independently C1-C6 alkyl. A polmacoxib intermediate is synthesized by using the compound. The compound disclosed by the invention is high in yield, low in cost, free of byproduct cyanogen compounds, safe, environment-friendly and suitable for industrialized production.

Description

[0001] This application is a divisional application of the earlier application. The filing date of the earlier application is: August 21, 2015. The application number is: 201510516237X. The name of the invention is: acyl triazole compounds, acetophenone-substituted benzene Methyl sulfoxide compounds and their preparation methods and applications. Technical field [0002] The present invention relates to the field of intermediate compounds for chemical synthesis of drugs and preparation methods thereof. Specifically, the present invention relates to intermediate compounds for the preparation of pomacoxib (Polmacoxib) and preparation methods thereof. Background technique [0003] 2,2-Dimethyl-4-(3-fluorophenyl)-5-[4-(methylthio)phenyl]-3(2H)furanone (Compound 01) and 2,2-dimethyl -4-(3-Fluorophenyl)-5-[4-(methylsulfoxide)phenyl]-3(2H)furanone (compound 02) is a synthetic new anti-inflammatory drug pomacoxib (compound 03 ) is an important intermediate. [0004] [0005] Li...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/08C07D249/10C07D307/58
CPCC07C315/02C07C317/24C07D249/08C07D249/10C07D307/58
Inventor 金春华唐剑波王可迪朱勤丰
Owner NINGBO BESTDRUG PHARMA CO LTD
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