تفاعل #45730
ord-10b35e463ed443d2b0cd50bb67c59fcc
معادلة التفاعل
المتفاعلات
الكواشف
المذيبات
ظروف التفاعل
المعالجة
- 1درجة الحرارةAfter cooling to room temperature
- 2أخرىthe reaction liquid
- 3استخلاصThe aqueous layer was further extracted twice with ethyl acetate
- 4غسيلwashed with saturated brine
- 5تجفيفdried over anhydrous sodium sulfate
- 6أخرىThe insoluble matter was separated by filtration
- 7أخرىthe solvent was evaporated away
- 8أخرىthe resulting residue was purified by preparative TLC (eluent, chloroform:methanol=96:4)
- 9أخرىto obtain a roughly-purified product (211 mg, 74% for 2 steps) as a white solid
- 10أخرىThis was recrystallized from ethyl acetate and diisopropyl ether
الإجراء التجريبي
2-Cyclopropyl-6-(3,5-difluorophenyl)-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-176) (including impurities, estimated as 0.68 mmol) was dissolved in dimethyl sulfoxide (5 ml), then at room temperature, triethylamine (142 μl, 1.02 mmol) and (3S)-3-(dimethylamino)pyrrolidine (112 μl, 0.88 mmol) were added, the solution was stirred under nitrogen atmosphere at 90° C. for 15 hours. After cooling to room temperature, the reaction liquid 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, then the solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=96:4) to obtain a roughly-purified product (211 mg, 74% for 2 steps) as a white solid. This was recrystallized from ethyl acetate and diisopropyl ether to obtain the entitled compound (46 mg) as a white solid.