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

HRID 17555Notes

Reaction equation

HRID 17555 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C(Cl)(Cl)Cl.[NH2:12][C:13]1[C:18]([NH2:19])=[C:17]([N:20]2[CH2:24][CH2:23][C@H:22]([N:25]([CH3:27])[CH3:26])[CH2:21]2)[C:16]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:15]([CH3:34])[C:14]=1[C:35]#[N:36]>O>[NH2:12][C:13]1[C:14]([C:35]#[N:36])=[C:15]([CH3:34])[C:16]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[C:17]([N:20]2[CH2:24][CH2:23][C@H:22]([N:25]([CH3:27])[CH3:26])[CH2:21]2)[C:18]=1[NH:19][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 62493Pivaloyl chlorideHCID 866308764,5-Diamino-6-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-2-methylbiphenyl-3-carbonitrile

Product 1

HCID 86630877N-[4-Amino-5-cyano-2-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-6-methylbiphenyl-3-yl]-2,2-dimethylpropionamideYield 43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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.

Workup

  1. customthe reaction
  2. extractionfollowed by extraction with chloroform
  3. washThe organic layer was washed with an aqueous saturated sodium hydrogencarbonate solution and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated away under reduced pressure
  6. washeluted with a mixed solvent of chloroform/methanol (95:5

Sources & evidence

ORD record
ord-3ec1a66659864c1384b987eaee51beef
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

Loading…