Reaktion #45887

Reaktionsgleichung

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

triethylamine

(3S)-3-(dimethylamino)pyrrolidine

→

compound

Ausbeute 46.1%

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

Ausbeute 46.1%

Lösungsmittel

dimethyl sulfide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooled
2. 2
   Einengenthis was concentrated under reduced pressure
3. 3
   workup.ADDITIONdiluted with chloroform
4. 4
   Waschenwashed with saturated brine
5. 5
   TrocknenThe organic layer was dried over anhydrous magnesium sulfate
6. 6
   Sonstigethe solvent was evaporated away under reduced pressure
7. 7
   SonstigeThe resulting residue was purified by preparative TLC (eluent, chloroform

Vorschrift

2-Cyclopropyl-7-fluoro-6-isopropenyl-5-methyl-1,3-benzoxazole-4-carbonitrile (I-315) (34 mg, 0.13 mmol) was dissolved in dimethyl sulfide (2 ml), then triethylamine (38 μl, 0.27 mmol) and (3S)-3-(dimethylamino)pyrrolidine (36 μl, 0.28 mmol) were added, followed by stirring under nitrogen atmosphere at 90° C. for 4 hours. After cooled, this was concentrated under reduced pressure, diluted with chloroform and washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated away under reduced pressure. The resulting residue was purified by preparative TLC (eluent, chloroform:methanol=10:1, v/v) to obtain the entitled compound (21 mg, 25%) as a brown crystal.

Quelle