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Acyl triazole compounds, acetophenone-substituted phenylmethyl sulfoxide compounds, preparation methods and applications thereof

A technology of phenylmethyl sulfoxide and acyl triazole, which is applied in the preparation of intermediate compounds of pomacoxib and its preparation field, can solve the problems of only 33% yield, high toxicity and poor effect

Active Publication Date: 2017-09-01
NINGBO BESTDRUG PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] 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
[0010] It has also been reported that 2-bromoisobutyryl bromide (compound 05) has been 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 compounds, acetophenone-substituted phenylmethyl sulfoxide compounds, preparation methods and applications thereof
  • Acyl triazole compounds, acetophenone-substituted phenylmethyl sulfoxide compounds, preparation methods and applications thereof
  • Acyl triazole compounds, acetophenone-substituted phenylmethyl sulfoxide compounds, preparation methods and applications 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, an acetophenone-substituted phenyl methyl sulfoxide compound and preparing methods and application thoseof. The structural formula (1) of the acyl triazole compound is as shown in the specification. In the structural formula (1), X is Cl or Br or I or OSO2R3; the R3 is C1-C4 alkyl groups or phenyl groups or substituted phenyl groups; the R1 and R2 separately are H or halogen or CN or NO2 or C1-C6 alkyl groups or C1-C6 alkoxy or C1-C6 alkyl sulphanyl or NR4R5, the R4 and R5 separately are C1-C6 alkyl groups. Polmacoxib midbody is formed by means of the compounds in a synthesis mode, and the compounds are high in yield, low in cost, free of byproduct cyanogen compound, safe, environmentally friendly and suitable for industrial production.

Description

technical field [0001] 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 [0002] 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. [0003] [0004] Literature reports: compound 02 is obtained by oxidation of compound 01, and compound 01 is obtained by cyclization of the compound of structural formula VII: [0005] [0006] The cyclizing agent used is 2-bromoisobutyrylonitrile (compound 04) (Bioorg.Med.Chem.2002, 10:1137-42; CN201410364152.X; WO2015080435), [0007] [0008] There are two disadvantages in this reaction: (1...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/08C07D249/10C07C317/24C07C315/02C07D307/58
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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