تفاعل #45647

معادلة التفاعل

ethyl acetate

triethylamine

(3S)-3-(dimethylamino)pyrrolidine

7-Fluoro-2-(1-hydroxy-1-methylethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

→

compound

المردود 93.3%

7-[(3S)-3-(Dimethylamino)pyrrolidin-1-yl]-2-(1-hydroxy-1-methylethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

المردود 93.3%

المذيبات

brine

dimethyl sulfoxide

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled to room temperature
2. 2
   أخرىThe aqueous layer was separated
3. 3
   استخلاصthis was extracted twice with ethyl acetate
4. 4
   غسيلthis was washed 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=9:1)

الإجراء التجريبي

7-Fluoro-2-(1-hydroxy-1-methylethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-112) (35 mg, 0.11 mmol) was dissolved in anhydrous dimethyl sulfoxide (2 ml), and at room temperature, triethylamine (24 μl, 0.17 mmol) and (3S)-3-(dimethylamino)pyrrolidine (22 μl, 0.17 mmol) were added. This mixture liquid was stirred at 90° C. for 12 hours, then cooled to room temperature. This was fractionated with ethyl acetate and saturated brine. The aqueous layer was separated, and this was extracted twice with ethyl acetate. The organic layers were combined, this was washed with saturated brine, dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=9:1) to obtain the entitled compound (41.5 mg, 91%) as a white solid. This was further recrystallized from hexane/diethyl ether to obtain a cream powder (27.5 mg).

المصدر