Carboxamide compound and preparation method and application thereof
A compound and thiazole technology, applied in the field of thiazole amide compounds and their preparation, can solve the problems of high cost of synthesis of brassinolide, no physiological activity, easy metabolic inactivation, etc., to improve the ability to resist lodging and have high promotion value , easy to prepare effects
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Embodiment 1
[0060] Embodiment 1, the preparation of compound 1a:
[0061] The reaction scheme is shown in the following formula:
[0062]
[0063] In a 100mL round-bottomed flask, add 2-aminothiazole (10mmol) and succinic anhydride (12mmol), stir and dissolve 15mL tetrahydrofuran (solvent A), heat up and reflux for 2 hours for acylation reaction, cool down to precipitate a solid, and filter to obtain a solid. Purified by ethanol recrystallization. The specific method of recrystallization is: add 3 mL of ethanol dropwise to 1 g of the primary product to be recrystallized, heat to reflux until the primary product is completely dissolved, and continue to reflux for 10 minutes, then slowly cool down to precipitate a solid, and filter with suction to obtain a pure product.
Embodiment 2
[0064] Embodiment 2, the preparation of compound 1b:
[0065] The reaction scheme is shown in the following formula:
[0066]
[0067]In a 100mL round-bottomed flask, add 2-aminothiazole (10mmol), succinic anhydride (12mmol), 15mL tetrahydrofuran and stir to dissolve, reflux for 3h for acylation reaction, cool down to precipitate a solid, filter to obtain a solid, and ethanol recrystallization for purification get intermediate products. Take the intermediate product (10mmol), dissolve it in 3ml of methanol, cool it to 0°C in an ice-salt bath, add 5ml of THF solution that has been prepared to obtain thionyl chloride dropwise at a constant temperature, and complete the dropwise addition in 30 minutes; continue to react for 5 hours, and pour the reaction mixture into 150mL In ice water, extracted with ethyl acetate (3x100mL), washed with saturated brine (3x100mL), anhydrous Na 2 SO 4 After drying, concentration by filtration, the crude product was purified by recrystallizat...
Embodiment 3
[0068] Embodiment 3, the preparation of compound 1d:
[0069] The reaction scheme is shown in the following formula:
[0070]
[0071] In a 100mL round bottom flask, add 2-aminothiazole (10mmol), 3mL (20mmol) triethylamine, 15ml tetrahydrofuran and stir to dissolve, then add TBTU (3.531g, 11mmol) and Boc-amino acid (10mmol). The reaction mixture was stirred at room temperature for acylation reaction for 12 h, and the progress of the reaction was detected by TLC. After the reaction, concentrate and dissolve with dichloromethane (50mL), adjust pH to 10 with 1M NaOH, after the system is separated, take the aqueous phase, acidify to pH=3 with 1M HCl, extract with ethyl acetate (3×100mL), wash with saturated brine ( 3x100mL), anhydrous Na 2 SO 4 After drying, concentration by filtration, the crude product was purified by recrystallization from ethanol. The specific method of recrystallization is: add 3 mL of ethanol dropwise to 1 g of the primary product to be recrystallized...
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