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Preparation method of thienopyridine ketone compounds

A compound, pyridone technology, applied in the field of preparation of thienopyridone compounds, can solve the problems of limited application range and many synthesis steps, and achieve the effects of wide application range, simple synthesis method and mild conditions

Active Publication Date: 2012-10-24
CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These thienopyridone compounds are all synthesized by ring formation of thiophene compounds. There are many synthesis steps, and different synthesis methods need to be selected according to different substituent groups, and the scope of application is limited.

Method used

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  • Preparation method of thienopyridine ketone compounds
  • Preparation method of thienopyridine ketone compounds
  • Preparation method of thienopyridine ketone compounds

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preparation example Construction

[0029] The invention provides a preparation method of thienopyridone compounds, which comprises the following steps: distilling 2-amino-3-acetylthiophene compounds with the structure of formula (I) and N,N-dimethylformamide Methyl acetal reaction to obtain thienopyridone compounds with the structure of formula (II).

[0030]

[0031] Among them, R 1 -H, -A, -COA, -CONA 2 , -COAr, -SO 2 A. -SO 2 Ar, -Ar, or -Het; R 2 -COA, -COAr, -COOA, -Ar or -Het; said A is C1~C30 chain alkyl, C1~C30 substituted chain alkyl or C3~C7 cycloalkyl; said Het is 1 Monocyclic unsaturated heterocycles with ~4 heteroatoms, bicyclic unsaturated heterocycles with 1 to 4 heteroatoms, substituted monocyclic unsaturated heterocycles with 1 to 4 heteroatoms or 1 to 4 heteroatoms A substituted bicyclic unsaturated heterocycle, the heteroatom is one or more of N, O and S atoms. When Het is a bicyclic unsaturated heterocyclic ring or a substituted bicyclic unsaturated heterocyclic ring, the heteroatom...

Embodiment 1

[0055] At room temperature, mix and stir 10mmol acetylacetone, 20mmol anhydrous potassium carbonate and 30ml N,N-dimethylformamide (DMF), slowly add 10mmol phenylisothiocyanate, react for 2h, add 10mmolβ-bromobenzene Ethanone, after continuing to react for 2 hours, pour the reaction solution into saturated saline, extract three times with 20ml of dichloromethane, combine the organic phases, wash with 20ml of water three times, add 5g of anhydrous sodium sulfate to dry, filter, remove the organic solvent, pass through silica gel Column chromatography separated to obtain 2-anilino-3-acetyl-4-methyl-5-benzoylthiophene.

[0056] The preparation method of the 2-amino-3-acetylthiophene compound used in the following examples is the same as above, the difference is that the raw material isothiocyanate with the structure of formula (III) and β-bromo with the structure of formula (IV) Compounds are chosen differently.

[0057] 2-(4-Methoxyanilino)-3-acetyl-4-methyl-5-(4-nitrophenyl)th...

Embodiment 2

[0070] Add 2mmol of 2-anilino-3-acetyl-4-methyl-5-benzoylthiophene obtained in Example 1, 4mmol DMFDMA and 20ml DMF to a 50ml round bottom flask equipped with a reflux condenser and a stirrer , heated to 120°C under stirring conditions, and reacted for 2 hours, poured the reaction liquid into 100ml saturated saline, extracted twice with 30ml dichloromethane, combined the organic phases, washed twice with 30ml water, added 5g anhydrous sulfuric acid Sodium drying, filtration, removal of organic solvent, separation by silica gel column chromatography to obtain 2-benzoyl-3-methyl-7-phenylthieno[2,3-b]pyridin-4[7H]ketone, yield 90%. The reaction formula is as follows:

[0071]

[0072] The 2-benzoyl-3-methyl-7-phenylthieno[2,3-b]pyridin-4[7H]ketone obtained in Example 2 is analyzed by nuclear magnetic resonance to obtain its hydrogen spectrum and carbon Spectrum, the result is as follows:

[0073] 1 H NMR (300MHz, CDCl 3 ): δ2.66(s,3H),6.39(d,J=7.8Hz,1H),7.44–7.60(m,9H),7....

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Abstract

The invention provides a preparation method of thienopyridine ketone compounds. 2-amino-3-acetyl thiophene compound having the structure of formula (I) and N,N-dimethylformamide dimethylacetal are used as raw materials to react to obtain the thienopyridine ketone compounds having the structure of formula (II). Compared with the existing technology of cyclization reaction of thiophene compounds, the method uses N,N-dimethylformamide dimethylacetal to conduct condensation reaction with 3-acetyl contained in the 2-amino-3-acetyl thiophene compound firstly, then to conduct intramolecular substitution reaction with 2-amino contained in the 2-amino-3-acetyl thiophene compound to form ring, so that the thienopyridine ketone compounds are synthesized in one step. The method provided by the invention has the advantages of simplicity and mild condition; Furthermore, R1 and R2 can be a variety of different substituent groups, having wide range of application.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a preparation method of thienopyridone compounds. Background technique [0002] Thienopyridine compounds are one of the most popular heterocyclic compounds researched at home and abroad. This type of compound has been widely used in the dye industry, and it also has good curative effects in sterilization, anti-tumor and cancer, and can be used as a sedative. medicines and medicines for high blood pressure, asthma, diabetes, ulcer disease and neurological diseases. [0003] Among them, thienopyridone compounds are organic compounds that widely exist in natural products, and most of them have important biological and pharmaceutical activities, such as: thieno[2,3-b]pyridine-6(7H)- Ketone derivatives can be used as kinase inhibitors, thienopyridone carboxamide can be used to treat diseases caused by malignant tumors, autoimmunity or pathological inflammation, and the commercialized...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04
Inventor 董德文张睿梁永久
Owner CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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