Pivaloyl chloride → N-(3-amino-2,4-difluoro-benzyl)-2,2-dimethyl-propionamide

HRID 1189617Notes

Reaction equation

HRID 1189617 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[NH2:8][C:9]1[C:10]([F:18])=[C:11]([CH:14]=[CH:15][C:16]=1[F:17])[CH2:12][NH2:13].C([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O>[NH2:8][C:9]1[C:10]([F:18])=[C:11]([CH:14]=[CH:15][C:16]=1[F:17])[CH2:12][NH:13][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 62493Pivaloyl chlorideHCID 516892Sodium BicarbonateHCID 568399693-Amino-2,4-difluoro-benzylamine

Product 1

HCID 56839977N-(3-amino-2,4-difluoro-benzyl)-2,2-dimethyl-propionamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

TEA (400 μL, 2.86 mmol) followed by pivaloyl chloride (60 μL, 0.52 mmol) are added to 3-amino-2,4-difluoro-benzylamine (120 mg as HCl salt) in THF (10 mL) and the mixture is stirred at rt overnight. The reaction mixture is diluted with EtOAc and sat NaHCO3-solution, the organic layer is washed with water and brine, dried and concentrated to give the sub-title compound.

Workup

  1. washthe organic layer is washed with water and brine
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7692ee36298944bcb0c4d9b7511b95db
Source dataset
uspto-grants-2014_03
Patent number
US08674113B2

Reaction notes

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