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

HRID 1260887Notes

Reaction equation

HRID 1260887 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:21]=[C:22]([CH2:26][NH2:27])[CH:23]=[CH:24][CH:25]=1)(=[O:19])=[O:18].C(N(CC)CC)C>CO.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:22]2[CH:23]=[CH:24][CH:25]=[C:20]([S:17]([CH3:16])(=[O:19])=[O:18])[CH:21]=2)[CH:10]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 5417922-Cyano-2-(3,4-dichloro-5(2H)-oxo-2-furyl)acetamideHCID 447171423-(Methylsulfonyl)benzylamine hydrochloride

Product 1

HCID 686623945-Chloro-2-imino-1-[3-(methylsulfonyl)benzyl]-1,2-dihydropyridine-3-carboxamide hydrochlorideYield 19.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a solution of 2-cyano-2-(3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)acetamide (0.5 g) in methanol (5 ml) was added a solution (3 ml) of 1-[3-(methylsulfonyl)phenyl]methanamine hydrochloride (1.4 g) and triethylamine (0.9 ml) in ethanol at room temperature, and the mixture was stirred for 24 hr. The reaction solvent was evaporated under reduced pressure, DMSO (5 ml) was added, and the mixture was stirred at 80° C. for 4 hr. The solvent was evaporated under reduced pressure and partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=4/1-1/0). 2N Hydrochloric acid-methanol solution (1 ml) was added to the obtained yellow oil at room temperature, and the precipitated crystals were filtered and recrystallized to give the title compound (78 mg).

Workup

  1. customThe reaction solvent was evaporated under reduced pressure, DMSO (5 ml)
  2. additionwas added
  3. stirringthe mixture was stirred at 80° C. for 4 hr
  4. customThe solvent was evaporated under reduced pressure
  5. custompartitioned between ethyl acetate and water
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=4/1-1/0)
  9. addition2N Hydrochloric acid-methanol solution (1 ml) was added to the obtained yellow oil at room temperature
  10. filtrationthe precipitated crystals were filtered
  11. customrecrystallized

Sources & evidence

ORD record
ord-b2491f856d1d40ccae843eafc9b25048
Source dataset
uspto-grants-2013_06
Patent number
US08470859B2

Reaction notes

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