Реакция #45658

Уравнение реакции

dimethyl sulfoxide

(3S)-3-(dimethylamino)pyrrolidine

dimethyl sulfoxide

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

triethylamine

→

compound

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

Растворители

brine

Условия реакции

Обработка

1. 1
   ТемператураAfter cooling
2. 2
   Другоеthe reaction liquid
3. 3
   Экстракцияwas extracted with ethyl acetate
4. 4
   Сушкаdried over anhydrous magnesium sulfate
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеthe filtrate was concentrated under reduced pressure

Методика

Under nitrogen atmosphere, a dimethyl sulfoxide (700 μl) solution of (3S)-3-(dimethylamino)pyrrolidine (24 μl, 192 μmol) was added at 150° C. to a dimethyl sulfoxide (2.5 ml) solution of 7-fluoro-5-methyl-6-phenyl-2-(piperidin-1-ylcarbonyl)-1,3-benzoxazole-4-carbonitrile (I-117) (58 mg, 160 μmol) and triethylamine (29 μl, 208 μmol), followed by stirring at the same temperature for 75 minutes. After cooling, saturated brine was added to the reaction liquid, and the reaction liquid was extracted with ethyl acetate. Next, the obtained organic layers were combined, 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 a crude product of the entitled compound as a solid, and the solid was recrystallized from diisopropyl ether/n-hexane to obtain the entitled compound (23 mg, 31%) as a pale yellow solid.

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