تفاعل #45660

معادلة التفاعل

ethyl acetate

triethylamine

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

dimethyl sulfoxide

(3S)-3-(dimethylamino)pyrrolidine

dimethyl sulfoxide

→

compound

المردود 67.0%

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

المردود 67.0%

المذيبات

brine

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added all at a time
2. 2
   درجة الحرارةThe mixture liquid was cooled to room temperature
3. 3
   غسيلThe organic layer was washed with saturated brine
4. 4
   تجفيفdried over anhydrous sodium sulfate
5. 5
   أخرىThe insoluble matter was separated by filtration
6. 6
   أخرىthe solvent was evaporated away
7. 7
   أخرىthe resulting residue was purified by preparative TLC (eluent, chloroform:methanol=9:1)

الإجراء التجريبي

7-Fluoro-5-methyl-2-(morpholin-4-ylcarbonyl)-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-118) (40 mg, 0.11 mmol) was dissolved in dimethyl sulfoxide (2 ml), and at room temperature, triethylamine (20 μl, 0.14 mmol) was added. Next, the solution was heated at 150° C., and a solution of (3S)-3-(dimethylamino)pyrrolidine (17 μl, 0.13 mmol) dissolved in dimethyl sulfoxide (0.5 ml) was added all at a time, followed by further stirring for 1 hour. The mixture liquid was cooled to room temperature, then this was fractionated with ethyl acetate and saturated brine. The organic layer was 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 preparative TLC (eluent, chloroform:methanol=9:1) to obtain the entitled compound (33.7 mg, 67%) as a yellow gel.

المصدر