Reaction #45833

Reaction equation

pivaloyl chloride

chloroform

4,5-diamino-6-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-2-methylbiphenyl-3-carbonitrile

→

compound

Yield 43.0%

N-[4-Amino-5-cyano-2-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-6-methylbiphenyl-3-yl]-2,2-dimethylpropionamide

Yield 43.0%

Solvents

water

Conditions

Workup

1. 1
   Otherthe reaction
2. 2
   Extractionfollowed by extraction with chloroform
3. 3
   WashThe organic layer was washed with an aqueous saturated sodium hydrogencarbonate solution and saturated brine
4. 4
   Dryingdried over anhydrous sodium sulfate
5. 5
   OtherThe solvent was evaporated away under reduced pressure
6. 6
   Washeluted with a mixed solvent of chloroform/methanol (95:5

Procedure

With cooling with ice, pivaloyl chloride (0.46 ml, 3.73 mmol) was dropwise added to a chloroform (40 ml) solution of 4,5-diamino-6-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-2-methylbiphenyl-3-carbonitrile (I-269) (1.25 g, 3.73 mmol). After stirring for 3 hours, water was added to the reaction liquid to stop the reaction, followed by extraction with chloroform. The organic layer was washed with an aqueous saturated sodium hydrogencarbonate solution and saturated brine, then dried over anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, then the residue was subjected to column chromatography, and eluted with a mixed solvent of chloroform/methanol (95:5, v/v) to obtain the entitled compound (675 mg, 43%) as a brown amorphous substance.

Source