Methyl iodide → 5-bromo-N,N,1-trimethyl-6-oxo-1,6-dihydropyridine-3-carboxamide

HRID 58047Notes

Reaction equation

HRID 58047 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[NH:6][CH:5]=[C:4]([C:9]([N:11]([CH3:13])[CH3:12])=[O:10])[CH:3]=1.IC.[C:16](=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH3:16])[CH:5]=[C:4]([C:9]([N:11]([CH3:13])[CH3:12])=[O:10])[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 897817475-bromo-N,N-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Product 1

HCID 897835395-bromo-N,N,1-trimethyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 5-bromo-N,N-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxamide (100 mg, 0.408 mmol) and iodomethane (57.9 mg, 0.408 mmol) in DMSO (3 mL) was added potassium carbonate (56.4 mg, 0.408 mmol). The mixture was stirred at room temperature overnight, filtered, and purified via preparative HPLC, eluting with a gradient of 10-90% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA). The product was dried under vacuum to give the title compound.

Workup

  1. filtrationfiltered
  2. custompurified via preparative HPLC
  3. washeluting with a gradient of 10-90% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA)
  4. customThe product was dried under vacuum

Sources & evidence

ORD record
ord-ccb0f21f6b3842d49e620e2e70932de7
Source dataset
uspto-grants-2016_09
Patent number
US09434743B2

Reaction notes

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