A formanilide compound containing 1,3,4-oxadiazole structure and its preparation method and application
A formanilide and compound technology, applied in the field of formanilide compounds and their preparation
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example 1
[0043] Example 1: 3-bromo-N-(2-methyl-4-bromo-6-(5-(thiophen-2-yl)-1,3,4-oxadiazol-2-yl)phenyl)- Preparation of 1-(3-chloropyridin-2-yl)-1H-pyrrole-5-carboxamide
[0044] In a 100mL single-necked bottle, the intermediate 6-bromo-2-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrrole-5-y1)-8-methyl-4H-3 , 1-benzoxazin-4-one (1.00g, 2.01mmol) and 2-thiophene hydrazide (0.35g, 2.42mmol) were dissolved in N,N-dimethylformamide (DMF), stirred at room temperature for 15min , then add sodium hydroxide (0.04g, 1.00mmol) and continue to stir, react for 2h, TLC point plate tracking, after the raw material point disappears, add triethylamine (0.61g, 6.03mmol) and add p-toluenesulfonate under ice-bath conditions Anhydride (1.15 g, 6.03 mmol). After reacting at room temperature for 2 hours, the reaction solution was poured into 500 mL of saturated sodium bicarbonate solution, stirred for 0.5 h, the solid was filtered, dried, and purified by column chromatography.
example 2
[0045] Example 2: 3-bromo-N-(4-chloro-2-(5-(5-chlorothien-2-yl)-1,3,4-oxadiazol-2-yl)-6-methylbenzene Preparation of -1-(3-chloropyridin-2-yl)-1H-pyrrole-5-carboxamide
[0046] In a 100mL single-necked bottle, the intermediate 2-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrrol-5-yl)-6-chloro-8-methyl-4H-3 , 1-Benzoxazin-4-one (1.00 g, 2.21 mmol) and 5-chlorothiophene-2-hydrazide (0.47 g, 2.65 mmol) were dissolved in N,N-dimethylformamide (DMF) , stirred at room temperature for 15min, then added sodium hydroxide (0.04g, 1.00mmol) and continued to stir, reacted for 2h, followed by TLC spot plate, after the raw material point disappeared, added triethylamine (0.67g, 6.63mmol) and under ice-bath conditions Add p-toluenesulfonic anhydride (1.27 g, 6.64 mmol). After reacting at room temperature for 2 hours, the reaction solution was poured into 300 mL of saturated sodium bicarbonate solution, stirred for 0.5 h, the solid was filtered, dried, and purified by column chromatography.
example 3
[0047] Example 3: 3-bromo-N-(4-chloro-2-(5-(5-cyanothiophen-2-yl)-1,3,4-oxadiazol-2-yl)-6-methyl Preparation of phenyl)-1-(3-chloropyridin-2-yl)-1H-pyrrole-5-carboxamide
[0048] In a 100mL single-necked bottle, the intermediate 2-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrrol-5-yl)-6-chloro-8-methyl-4H-3 , 1-Benzoxazin-4-one (1.00 g, 2.21 mmol) and 5-cyanothiophene-2-hydrazide (0.44 g, 2.65 mmol) were dissolved in N,N-dimethylformamide (DMF) , stirred at room temperature for 15min, then added sodium hydroxide (0.04g, 1.00mmol) and continued to stir, reacted for 2h, followed by TLC spot plate, after the raw material point disappeared, added triethylamine (0.67g, 6.63mmol) and placed in an ice bath p-Toluenesulfonic anhydride (1.27 g, 6.64 mmol) was added at the same time. After reacting at room temperature for 2 hours, the reaction solution was poured into 500 mL of saturated sodium bicarbonate solution, stirred for 0.5 h, the solid was filtered, dried, and purified by column c...
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