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

HRID 1258695Notes

Reaction equation

HRID 1258695 reaction equation
[NH2:1][C:2]1[C:3]([F:11])=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH2:5][NH2:6].[C:12](Cl)(=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14]>C1COCC1.CCOC(C)=O>[NH2:1][C:2]1[C:3]([F:11])=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH2:5][NH:6][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 2

HCID 62493Pivaloyl chlorideHCID 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 (1.92 mL, 13.8 mmol) was added to a mixture of 3-amino-2,4-difluoro-benzylamine (0.58 g, 2.5 mmol) in THF (40 ml) followed by pivaloyl chloride (0.31 mL, 2.5 mmol) and it was stirred overnight. The mixture was diluted with EtOAc, washed successively with satd. NaHCO3 and brine. The organic phase was dried with Na2SO4, filtered and concentrated.

Workup

  1. washwashed successively with satd
  2. dry with materialThe organic phase was dried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-28c837cfacc347ef8c0c80b0a3aad014
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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