تفاعل #45596

معادلة التفاعل

Triethylamine

(3S)-3-(dimethylamino)pyrrolidine

dimethyl sulfoxide

2-[2-(benzyloxy)-1,1-dimethylethyl]-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

→

compound

المردود 91.1%

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

المردود 91.1%

المذيبات

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter cooling
2. 2
   أخرىthe reaction liquid
3. 3
   غسيلwashed three times with saturated brine
4. 4
   تجفيفdried over anhydrous magnesium sulfate
5. 5
   تركيزconcentrated under reduced pressure
6. 6
   أخرىThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:1)

الإجراء التجريبي

Triethylamine (222 μl, 1.59 mmol), (3S)-3-(dimethylamino)pyrrolidine (152 μl, 1.19 mmol) were added to a dimethyl sulfoxide (16.5 ml) solution of 2-[2-(benzyloxy)-1,1-dimethylethyl]-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-66) (330 mg, 0.796 mmol), followed by stirring overnight at 90° C. After cooling, the reaction liquid was diluted with ethyl acetate, washed three times with saturated brine, then dried over anhydrous magnesium sulfate, concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:1) to obtain the entitled compound (369 mg, 91%) as a pale brown oil.

المصدر