تفاعل #45775

معادلة التفاعل

(3S)-3-(dimethylamino)pyrrolidin

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

triethylamine

→

compound

المردود 53.0%

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

المردود 53.0%

المذيبات

dimethyl sulfoxide

dimethyl sulfoxide

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter cooling
2. 2
   أخرىthe solvent was evaporated away under reduced pressure
3. 3
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
4. 4
   غسيلThe organic layer was washed with saturated brine
5. 5
   استخلاصthe aqueous layer was extracted with ethyl acetate
6. 6
   workup.ADDITIONNext, saturated sodium hydrogencarbonate water was added to the aqueous layer
7. 7
   استخلاصfollowed by extraction with chloroform
8. 8
   تجفيفThe combined organic layer was dried over anhydrous magnesium sulfate
9. 9
   ترشيحfiltered
10. 10
    تركيزthe filtrate was concentrated under reduced pressure

الإجراء التجريبي

Under nitrogen atmosphere at 140 to 150° C., a dimethyl sulfoxide (1 ml) solution of (3S)-3-(dimethylamino)pyrrolidin (86 μl, 679 μmol) was added to a dimethyl sulfoxide (10 ml) solution of N-(1-acetylpyrrolidin-3-yl)-4-cyano-7-fluoro-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide (I-206) (238 mg, 566 μmol) and triethylamine (103 μl, 736 μmol), followed by stirring at the same temperature for 45 minutes. After cooling, the solvent was evaporated away under reduced pressure, the residue was dissolved in ethyl acetate. The organic layer was washed with saturated brine, then the aqueous layer was extracted with ethyl acetate. Next, saturated sodium hydrogencarbonate water was added to the aqueous layer, followed by extraction with chloroform. The combined organic layer was dried over anhydrous magnesium sulfate, then 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 (10:1, v/v) gave the entitled compound (153 mg, 53%) as an amorphous substance.

المصدر