Potassium Carbonate → 5-Chloro-2-imino-1-[2-(methylsulfonyl)benzyl]-1,2-dihydropyridine-3-carboxamide hydrochloride

HRID 447865Notes

Reaction equation

HRID 447865 reaction equation
[C:1]([CH:3]([CH:7]1[C:11]([Cl:12])=[C:10](Cl)C(=O)O1)[C:4]([NH2:6])=[O:5])#[N:2].Cl.[CH3:16][S:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][NH2:27])(=[O:19])=[O:18].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>C(O)C>[ClH:12].[Cl:12][C:11]1[CH:7]=[C:3]([C:4]([NH2:6])=[O:5])[C:1](=[NH:2])[N:27]([CH2:26][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[S:17]([CH3:16])(=[O:19])=[O:18])[CH:10]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 5417922-Cyano-2-(3,4-dichloro-5(2H)-oxo-2-furyl)acetamideHCID 162183342-(Methanesulfonyl)benzylamine hydrochloride

Product 1

HCID 669701345-Chloro-2-imino-1-[2-(methylsulfonyl)benzyl]-1,2-dihydropyridine-3-carboxamide hydrochlorideYield 20.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Cyano-2-(3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)acetamide (1.8 g), 1-[2-(methylsulfonyl)phenyl]methanamine hydrochloride (1.5 g) and potassium carbonate (1.8 g) were stirred in ethanol (30 ml) at 80° C. for 16 hr. The reaction mixture was poured into 1N aqueous sodium hydroxide solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and filtered. The solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate). The obtained residue was dissolved in methanol, 4N hydrogen chloride-ethyl acetate solution (2 ml) was added, and the mixture was crystallized from methanol-ethyl acetate. The precipitated crystals were collected by filtration, and recrystallized to give the title compound (0.29 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by basic silica gel column chromatography (ethyl acetate)
  7. dissolutionThe obtained residue was dissolved in methanol
  8. addition4N hydrogen chloride-ethyl acetate solution (2 ml) was added
  9. customthe mixture was crystallized from methanol-ethyl acetate
  10. filtrationThe precipitated crystals were collected by filtration
  11. customrecrystallized

Sources & evidence

ORD record
ord-5965ffc28f5244ab8bf3e1f3f10c1232
Source dataset
uspto-grants-2013_07
Patent number
US08481569B2

Reaction notes

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