Reaction #45887

Reaction equation

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

triethylamine

(3S)-3-(dimethylamino)pyrrolidine

→

compound

Yield 46.1%

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

Yield 46.1%

Solvents

dimethyl sulfide

Conditions

Workup

1. 1
   TemperatureAfter cooled
2. 2
   Concentrationthis was concentrated under reduced pressure
3. 3
   workup.ADDITIONdiluted with chloroform
4. 4
   Washwashed with saturated brine
5. 5
   DryingThe organic layer was dried over anhydrous magnesium sulfate
6. 6
   Otherthe solvent was evaporated away under reduced pressure
7. 7
   OtherThe resulting residue was purified by preparative TLC (eluent, chloroform

Procedure

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.

Source