تفاعل #45890

معادلة التفاعل

6-Amino-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile

2,5-dimethoxytetrahydrofuran

→

compound

المردود 81.0%

2-Cyclopropyl-7-fluoro-5-methyl-6-(pyrrol-1-yl)-1,3-benzoxazole-4-carbonitrile

المردود 81.0%

المذيبات

acetic acid

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled to room temperature
2. 2
   أخرىThe solvent was evaporated away under reduced pressure
3. 3
   استخلاصThe aqueous layer was further extracted twice with ethyl acetate
4. 4
   غسيلwashed with saturated brine
5. 5
   تجفيفdried over anhydrous sodium sulfate
6. 6
   أخرىThe insoluble matter was separated by filtration
7. 7
   أخرىthe solvent was evaporated away
8. 8
   أخرىthe resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

الإجراء التجريبي

6-Amino-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-319) (29 mg, 0.13 mmol) was dissolved in acetic acid (2 ml), then at room temperature, 2,5-dimethoxytetrahydrofuran (49 μl, 0.38 mml) was added. The solution was stirred at 100° C. for 3 hours, then cooled to room temperature. The solvent was evaporated away under reduced pressure, the resulting residue was fractionated with ethyl acetate and an aqueous saturated sodium hydrogencarbonate solution. The aqueous layer was further extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane:ethyl acetate=9:1, v/v) to obtain the entitled compound (28.5 mg, 81%) as a white solid.

المصدر