Reaktion #45661

Reaktionsgleichung

dimethyl sulfoxide

(3S)-3-(dimethylamino)pyrrolidine

dimethyl sulfoxide

2-[(4-acetylpiperazin-1-yl)carbonyl]-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

triethylamine

→

compound

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

Lösungsmittel

brine

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Sonstigethe reaction liquid
3. 3
   Extraktionwas extracted with ethyl acetate
4. 4
   WaschenNext, the combined organic layer was washed with saturated brine
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenthe filtrate was concentrated under reduced pressure

Vorschrift

Under nitrogen atmosphere, a dimethyl sulfoxide (2 ml) solution of (3S)-3-(dimethylamino)pyrrolidine (99 μl, 782 μmol) was added at 150° C. to a dimethyl sulfoxide (11 ml) solution of 2-[(4-acetylpiperazin-1-yl)carbonyl]-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-119) (265 mg, 652 μmol) and triethylamine (118 μl, 848 μmol), followed by stirring at the same temperature for 5 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 (10:1, v/v) gave a crude product of the entitled compound as a solid, and the solid was suspended and washed in diisopropyl ether to obtain the entitled compound (72 mg, 22%) as an amorphous substance.

Quelle