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General procedure: 2-Aminothiazoles (0.1 mol) were dissolved in the least amount of glacial acetic acid, and then bromine (0.11 mol) was added drop-wise with continuous stirring at room temperature. The mixture was heated at 80 °C for 90 min then stirred at room temperature for 12 h. The mixture was filtered and washed with water. The precipitate was heated in water, and the aqueous solution was alkalized by ammonia, filtered, washed with water and then dried. Crystals were formed from ethanol/water to give the 5-bromothiazol-2-amine compounds 3a–f.
Example 3 The Synthesis of Compound (2) [0105] At ?10° C., a solution of <strong>[1001-26-9]ethyl 3-ethoxyacrylate</strong> (14.4 g, 0.1 mol) in water/ dioxane (1:1) (100 mL) is treated with N-bromo-succinimide (19.6 g, 0.11 mol). The reaction mixture is stirred at room temperature for 1 hour, then thiourea (7.6 g, 0.1 mol) is added and the reaction mixture is heated to 80° C. for 1 hour. After the reaction solution is cooled to room temperature, aqueous ammonia (20 mL) is added therein. The paste produced is stirred at room temperature for 10 minutes, and filtered. The resultant filter cake is washed with water and dried under vacuum to give compound (2-1) (12.1 g, 70percent).
ethyl 2-(2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetamido)thiazole-4-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
41%
General procedure: A solution of <strong>[345637-71-0]2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid</strong> or 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid (4.57mmol), EDCI (1.05 g, 5.48 mmol), HOBT (0.65 g, 4.80 mmol) in anhydrous CH2Cl2 (20 mL) was stirred for 1 h at room temperature under nitrogen atmosphere, followed adding compound 1 (1.0 g,4.80 mmol) and Et3N (0.55 g, 5.48 mmol). The reaction was then stirred overnight at room temperature. After completion of the reaction, the mixture was washed with H2O (20mL), saturated NaHCO3 (20mL) and brine (20 mL), the organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatograph on silica gel (200-300mesh) by ethyl acetate and petroleum ether (v/v= 1:31:1) as eluent to afford target compounds (yield 41.0%-45.2%).
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