Reaktion #45753

Reaktionsgleichung

(3S)-3-(Dimethylamino)pyrrolidine

triethylamine

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

→

compound

Ausbeute 57.7%

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

Ausbeute 57.7%

Lösungsmittel

dimethyl sulfoxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction liquid
2. 2
   Einengenwas concentrated under reduced pressure
3. 3
   workup.DISSOLUTIONthe residue was dissolved in chloroform (50 ml)
4. 4
   Waschenwashed with saturated brine (50 ml)
5. 5
   TrocknenAfter drying over anhydrous sodium sulfate and concentration
6. 6
   Sonstigethe resulting residue was purified by preparative TLC (eluent, chloroform:methanol=10:1)

Vorschrift

(3S)-3-(Dimethylamino)pyrrolidine (67.9 μl, 0.535 mmol) and triethylamine (86.1 μl, 0.618 mmol) were added to a dimethyl sulfoxide (5 ml) solution of 7-fluoro-5-methyl-2-(4-methyl-3-oxopiperazin-1-yl)-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-188) (150 mg, 0.412 mmol), followed by stirring in an oil bath at 130° C. for 3 hours. The reaction liquid was concentrated under reduced pressure, the residue was dissolved in chloroform (50 ml), washed with saturated brine (50 ml). After drying over anhydrous sodium sulfate and concentration, the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=10:1) to obtain the entitled compound (109 mg, 54.5%) as a colorless foamy substance.

Quelle