Reaktion #45725

Reaktionsgleichung

ethyl acetate

triethylamine

(3S)-3-(dimethylamino)pyrrolidine

2-Cyclopropyl-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

→

product

Ausbeute 69.0%

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

Ausbeute 69.0%

Lösungsmittel

brine

dimethyl sulfoxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction liquid
2. 2
   ExtraktionThe aqueous layer was further extracted twice with ethyl acetate
3. 3
   Waschenwashed with saturated brine
4. 4
   Trocknendried over anhydrous sodium sulfate
5. 5
   SonstigeThe insoluble matter was separated by filtration
6. 6
   Sonstigethe solvent was evaporated away
7. 7
   Sonstigethe resulting residue was purified by preparative TLC (eluent, chloroform:methanol=97:3)

Vorschrift

2-Cyclopropyl-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-173) (70 mg, 0.24 mmol) was dissolved in dimethyl sulfoxide (2 ml), then at room temperature, triethylamine (50 μl, 0.36 mmol) and (3S)-3-(dimethylamino)pyrrolidine (40 μl, 0.31 mmol) were added. After cooling to room temperature, the reaction liquid was fractionated with ethyl acetate and saturated brine. The aqueous layer was further extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, then the solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=97:3) to obtain a roughly-purified product (64 mg, 69%).

Quelle