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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 invention relates to the field of an intermediate compound of a chemically synthesized drug and a preparation method thereof. Specifically, the invention relates to an intermediate compound for preparing pomacoxib (Polmacoxib) and a preparation method 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 novel anti-inflammatory drug pomacib (compound 03 ) important intermediates. [0004] [0005] Literature reports: compound 02 is ...

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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