تفاعل #45634

معادلة التفاعل

ethyl acetate

triethylamine

(3S)-3-(dimethylamino)pyrrolidine

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

→

compound

المردود 35.0%

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

المردود 35.0%

المذيبات

water

dimethyl sulfoxide

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter cooling to room temperature
2. 2
   غسيلThe organic layer was washed with saturated brine
3. 3
   تجفيفdried over anhydrous sodium sulfate
4. 4
   أخرىThe solvent was evaporated away
5. 5
   غسيلeluted with a mixed solvent of chloroform/methanol (10:1
6. 6
   غسيلv/v), and washed with n-hexane and ethyl acetate

الإجراء التجريبي

7-Fluoro-2-(2-methoxy-1,1-dimethylethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-100) (40 mg, 0.12 mmol) was dissolved in dimethyl sulfoxide (0.8 ml), triethylamine (23 μl, 0.17 mmol) and (3S)-3-(dimethylamino)pyrrolidine (18 μl, 0.14 mmol) were added, followed by stirring at 90° C. for 3 hours under nitrogen atmosphere. After cooling to room temperature, ethyl acetate was added, followed by fractionation with water. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was evaporated away and the resulting residue was subjected to preparative thin-layer silica gel column chromatography, eluted with a mixed solvent of chloroform/methanol (10:1, v/v), and washed with n-hexane and ethyl acetate to obtain the entitled compound (18 mg, 35%) as a white solid.

المصدر