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

HRID 1015829Notes

Reaction equation

HRID 1015829 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][O:17][C:18]1[CH:19]=[CH:20][C:21]([S:26]([CH3:29])(=[O:28])=[O:27])=[C:22]([CH2:24][NH2:25])[CH:23]=1.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:25]([CH2:24][C:22]2[CH:23]=[C:18]([O:17][CH3:16])[CH:19]=[CH:20][C:21]=2[S:26]([CH3:29])(=[O:28])=[O:27])[CH:10]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 5417922-Cyano-2-(3,4-dichloro-5(2H)-oxo-2-furyl)acetamideHCID 66877686(5-Methoxy-2-(methylsulfonyl)phenyl)methanamine hydrochloride

Product 1

HCID 669695825-Chloro-2-imino-1-[5-methoxy-2-(methylsulfonyl)benzyl]-1,2-dihydropyridine-3-carboxamide hydrochlorideYield 84.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(Step 4) 2-Cyano-2-(3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)acetamide (2.33 g), 1-[5-methoxy-2-(methylsulfonyl)phenyl]methanamine hydrochloride obtained in Step 3 (3.0 g) and potassium carbonate (4.12 g) were stirred in ethanol (30 ml) at 85° C. for 16 hr. The reaction mixture was treated with 1N sodium hydroxide solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. 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, and 4N hydrogen chloride-ethyl acetate solution (4 ml) was added. The mixture was crystallized from methanol-ethyl acetate, and the precipitated crystals were collected by filtration, and recrystallized to give the title compound (1.7 g).

Workup

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

Sources & evidence

ORD record
ord-8d913cc818d4406a9cf7d65cb90dec8e
Source dataset
uspto-grants-2011_07
Patent number
US07985863B2

Reaction notes

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