تفاعل #45664

معادلة التفاعل

dimethyl sulfoxide

(3S)-3-(dimethylamino)pyrrolidine

dimethyl sulfoxide

4-cyano-7-fluoro-N-(2-methoxyethyl)-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide

triethylamine

→

compound

المردود 53.0%

4-Cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-N-(2-methoxyethyl)-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide

المردود 53.0%

المذيبات

brine

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter cooling
2. 2
   أخرىthe reaction liquid
3. 3
   استخلاصwas extracted with ethyl acetate
4. 4
   غسيلNext, the combined organic layer was washed with saturated brine
5. 5
   تجفيفdried over anhydrous magnesium sulfate
6. 6
   ترشيحfiltered
7. 7
   تركيزthe filtrate was concentrated under reduced pressure

الإجراء التجريبي

Under nitrogen atmosphere, a dimethyl sulfoxide (2 ml) solution of (3S)-3-(dimethylamino)pyrrolidine (70 μl, 552 μmol) was added at 150° C. to a dimethyl sulfoxide (7 ml) solution of 4-cyano-7-fluoro-N-(2-methoxyethyl)-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide (I-122) (169 mg, 460 μmol) and triethylamine (83 μl, 598 μmol), followed by stirring at the same temperature for 2 hours. After cooling, saturated brine was added to the reaction liquid, and the reaction liquid was extracted with ethyl acetate. Next, the combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography, and the eluate with dichloromethane/methanol (20:1, v/v) gave the entitled compound (112 mg, 53%) as an amorphous substance.

المصدر