Reaktion #45653

Reaktionsgleichung

dimethyl sulfoxide

(3R)-3-methylaminopyrrolidine

dimethyl sulfoxide

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

triethylamine

→

compound

Ausbeute 23.0%

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

Ausbeute 23.0%

Lösungsmittel

brine

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Sonstigethe reaction liquid
3. 3
   Extraktionwas extracted with chloroform
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 (3R)-3-methylaminopyrrolidine (85 μl, 660 μmol) was added at 150° C. to a dimethyl sulfoxide (11 ml) solution of 4-cyano-7-fluoro-N,N,5-trimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide (I-114) (180 mg, 557 μmol) and triethylamine (101 μl, 724 μmol), followed by stirring at the same temperature for 30 minutes. After cooling, saturated brine was added to the reaction liquid, and the reaction liquid was extracted with chloroform. 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 preparative silica gel column chromatography. The eluate with chloroform/methanol (10:1, v/v) gave the entitled compound (53 mg, 23%) as a white amorphous substance.

Quelle