تفاعل #45854

معادلة التفاعل

dimethyl sulfoxide

(3S)-3-(methylamino)pyrrolidine

dimethyl sulfoxide

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

triethylamine

→

compound

المردود 32.2%

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

المردود 32.2%

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 the reduced pressure
8. 8
   أخرىThe resulting residue was purified by preparative TLC (eluent, dichloromethane

الإجراء التجريبي

Under nitrogen atmosphere, a dimethyl sulfoxide (1 ml) solution of (3S)-3-(methylamino)pyrrolidine (67 μl, 633 μmol) was added at 140 to 150° C. to a dimethyl sulfoxide (10 ml) solution of 4-cyano-N-ethyl-7-fluoro-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide (I-285) (178 mg, 528 μmol) and triethylamine (96 μl, 686 μmol), followed by stirring at the same temperature for 160 minutes. 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, then dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under the reduced pressure. The resulting residue was purified by preparative TLC (eluent, dichloromethane:methanol=10:1, v/v) to obtain the entitled compound (71 mg, 32%) as an amorphous substance.

المصدر