Thiazole-5-carboxamide compound, its preparation method, pharmaceutical composition and application
A kind of compound, methyl technology, applied in thiazole-5-carboxamide compound, its preparation method and pharmaceutical composition and use field
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Embodiment 14
[0176] Example 14-Methyl-2-(4-trifluoromethylphenyl)-N-(5-methylisoxazol-3-yl)thiazole-5-carboxamide
[0177]
[0178] In a 50ml eggplant-shaped bottle, add 0.505g (1.76mmol) of 4-methyl-2-(4-trifluoromethylphenyl)-thiazole-5-carboxylic acid and 10mL of dichloromethane, add 0.8mL of oxalyl chloride ( 9.33mmol), stirred at room temperature, 2 drops of dimethylformamide was added dropwise, and a large amount of gas was generated immediately. After stirring for 2 hours, the reaction solution was completely clarified, and the unreacted oxalyl chloride was removed by distillation under reduced pressure to obtain a yellow solid 4-methyl- 2-(4-fluorophenyl)-N-(thiazol-2-yl)thiazole-5-carbonyl chloride.
[0179] Add 0.215 g (2.19 mmol) of 5-methyl-3-aminoisoxazole into a 50 mL eggplant-shaped bottle, add 10 mL of dichloromethane to dissolve, add 2.8 mL of triethylamine, and dissolve the acid chloride prepared in the previous step with 10 mL of dichloromethane Dissolve, add dropwis...
Embodiment 24
[0180] Example 24-Methyl-2-(4-trifluoromethylphenyl)-N-(pyridin-2-yl)thiazole-5-carboxamide
[0181]
[0182] Add 3.582g (38.06mmol) of 2-aminopyridine into a 250mL eggplant-shaped bottle, dissolve in 50mL dry tetrahydrofuran, and stir magnetically to obtain a light yellow clear liquid. Add 2.599 g of 60% sodium hydride powder in batches under cooling in an ice-water bath to generate bubbles and obtain a beige turbid liquid. Slowly add 12.0 g (38.06 mmol) of 4-methyl-2-(4-trifluoromethylbenzene base) ethyl thiazole-5-carboxylate dried tetrahydrofuran (20mL) solution, dripped for 30min, heated to reflux for 1.5h, followed by TLC until the reaction was basically completed, concentrated under reduced pressure to obtain a yellow solid, added dichloromethane (200mL), 1mol / Adjust the pH to 7 with L hydrochloric acid to fully dissolve the solid. Filter to remove insoluble matter, separate the liquids, extract the aqueous phase with dichloromethane (30ml×3), combine the organic p...
Embodiment 34
[0183] Example 34-Methyl-2-(4-fluorophenyl)-N-(5-methylpyridin-2-yl)thiazole-5-carboxamide
[0184]
[0185] Add 0.526 g (4.86 mmol) of 5-methyl-2-aminopyridine into a 100 mL three-necked flask, dissolve in 20 mL of dry tetrahydrofuran, and stir magnetically to obtain a pale yellow clear liquid. Add 0.340g (8.46mmol) of 60% sodium hydride powder in batches under cooling in an ice-water bath, and bubbles are generated to obtain a gray turbid liquid. Slowly add 1.230g (4.42mmol) of 4-methyl-2-(4-fluorophenyl) dropwise )-thiazole-5-carboxylic acid ethyl ester in dry tetrahydrofuran (10mL) solution, after 10 minutes of dripping, heated to reflux for 1 hour, the reaction solution first turned yellow, and finally turned reddish brown, TLC traced until the reaction was basically completed, concentrated to give brown yellow For the solid, add dichloromethane (30 mL) and 1 mol / L hydrochloric acid to adjust the pH to 7 to fully dissolve the solid. Filter to remove insoluble matter, ...
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