A kind of preparation method of 2,4,5-trisubstituted oxazole compounds
A compound, tri-substituted technology, applied in the field of organic synthesis
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Embodiment 1
[0057] Example 1: N 5 , Synthesis of 4 diphenyloxazole-2,5-diamine (3a)
[0058] Add (S)-2-amino-N,2-diphenylacetamide (226mg, 1mmol), potassium cyanate (162mg, 2mmol), 6mL water and 6mL methanol into a 25mL reaction vessel, stir and heat up to 50°C, Add 0.25mmol acetic acid, and stir the reaction at constant temperature for 3h. The reaction solution was cooled to room temperature, 15 mL of water was added, and cooled overnight at 2°C. The crystals were filtered and dried at 50°C to obtain the product N,2-diphenyl-2-ureidoacetamide. To a solution of anhydrous dichloromethane (4 mL) was added triphenylphosphine oxide (835 mg, 3 mmol) followed by slow addition of trifluoromethanesulfonic anhydride (250 μl, 1.5 mmol) at 0°C. The reaction mixture was stirred at 0 °C for 10 min, then adjusted to room temperature. Then N,2-diphenyl-2-ureidoacetamide (292 mg, 1 mmol) was added. After 1 h of reaction, the reaction mixture was quenched with 10% aqueous sodium bicarbonate. Extract...
Embodiment 2
[0061] Example 2: Synthesis of 2-((2-amino-4-phenyloxazol-5-yl)amino)benzoic acid methyl ester (3b) Add (S)-2-amino-N-( 2-methoxycarbonylphenyl)-2-phenylacetamide (284mg, 1mmol), potassium cyanate (243mg, 3mmol), 6mL of water and 6mL of methanol, stirred and heated to 50 ° C, added 0.25mmol of acetic acid, constant temperature The reaction was stirred for 4.5h. The reaction solution was cooled to room temperature, 15 mL of water was added, and cooled overnight at 2°C. The crystals were filtered and dried at 60°C to obtain the product (S)-2-amino-N-(2-methoxycarbonylphenyl)-2-phenylacetamide. To a solution of anhydrous dichloromethane (4 mL) was added triphenylphosphine oxide (557 mg, 2 mmol) followed by slow addition of trifluoromethanesulfonic anhydride (167 μl, 1 mmol) at 0°C. The reaction mixture was stirred at 0 °C for 10 min, then adjusted to room temperature. Then (S)-2-amino-N-(2-methoxycarbonylphenyl)-2-phenylacetamide (350 mg, 1 mmol) was added. After 2 h of react...
Embodiment 3
[0064] Example 3: 4-Phenyl N 5 Synthesis of -(2-(trifluoromethyl)phenyl)oxazole-2,5-diamine (3c)
[0065](S)-2-amino-N-(2-trifluoromethylphenyl)-2-phenylacetamide (293mg, 1mmol), potassium cyanate (324mg, 4mmol), 6mL of water and 6mL of methanol was stirred and the temperature was raised to 50°C, 0.25 mmol of acetic acid was added, and the reaction was stirred at constant temperature for 6h. The reaction solution was cooled to room temperature, 15 mL of water was added, and cooled overnight at 2°C. The crystals were filtered and dried at 70°C to obtain the product 2-phenyl-N-(2-(trifluoromethyl)phenyl)-2-ureidoacetamide. To a solution of anhydrous dichloromethane (4 mL) was added triphenylphosphine oxide (1113 mg, 4 mmol) followed by slow addition of trifluoromethanesulfonic anhydride (333 μl, 2 mmol) at 0°C. The reaction mixture was stirred at 0 °C for 10 min, then adjusted to room temperature. Then 2-phenyl-N-(2-(trifluoromethyl)phenyl)-2-ureidoacetamide (360 mg, 1 mmol)...
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