تفاعل #45732

معادلة التفاعل

sodium hydrogencarbonate

triethylamine

(3S)-3-(dimethylamino)pyrrolidine

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

→

product

المردود 85.4%

2-Cyclopropyl-6-(2,3-difluorophenyl)-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-1,3-benzoxazole-4-carbonitrile

المردود 85.4%

المذيبات

ethyl acetate

dimethyl sulfoxide

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter cooling to room temperature
2. 2
   أخرىthe reaction liquid
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 preparative TLC (eluent, chloroform:methanol=92:8)

الإجراء التجريبي

2-Cyclopropyl-6-(2,3-difluorophenyl)-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-177) (109 mg, 0.33 mmol) was dissolved in dimethyl sulfoxide (3 ml), then at room temperature, triethylamine (70 μl, 0.50 mmol) and (3S)-3-(dimethylamino)pyrrolidine (55 μl, 0.43 mmol) were added. The solution was stirred under nitrogen atmosphere at 90° C. for 23 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=92:8) to obtain a roughly-purified product (119 mg, 85%) as a white solid. This was recrystallized from diisopropyl ether to obtain the entitled compound (71 mg) as a white solid.

المصدر