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

HRID 1015812Notes

Reaction equation

HRID 1015812 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:19]1[CH:20]=[C:21]([CH2:25][NH2:26])[CH:22]=[CH:23][CH:24]=1)=[O:18].C(N(CC)CC)C>CO>[ClH:12].[Cl:12][C:11]1[CH:7]=[C:3]([C:4]([NH2:6])=[O:5])[C:1](=[NH:2])[N:26]([CH2:25][C:21]2[CH:22]=[CH:23][CH:24]=[C:19]([S:17]([CH3:16])=[O:18])[CH:20]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5417922-Cyano-2-(3,4-dichloro-5(2H)-oxo-2-furyl)acetamideHCID 668784001-[3-(Methylsulfinyl)phenyl]methanamine hydrochloride

Product 1

HCID 669697955-Chloro-2-imino-1-[3-(methylsulfinyl)benzyl]-1,2-dihydropyridine-3-carboxamide hydrochlorideYield 35.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
50 °C

Procedure

To a suspension of 2-cyano-2-(3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)acetamide (1.0 g) in methanol (10 ml) was added a solution of 1-[3-(methylsulfinyl)phenyl]methanamine hydrochloride (1.8 g) and triethylamine (2.4 ml) in methanol (5 ml) at room temperature, and the mixture was stirred overnight at 50° C. The reaction solvent was evaporated under reduced pressure, acetic acid (5 ml) was added, and the mixture was stirred at 50° C. for 2 hr. The solvent was evaporated under reduced pressure, the residue was partitioned with ethyl acetate, 1N aqueous sodium hydroxide solution and aqueous sodium bicarbonate, and the organic layer was dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=7:3→1:0). 4N Hydrochloride-ethyl acetate solution (1 ml) was added to the obtained yellow oil, and the precipitated crystals were collected by filtration, and recrystallized to give the title compound (270 mg).

Workup

  1. customThe reaction solvent was evaporated under reduced pressure, acetic acid (5 ml)
  2. additionwas added
  3. stirringthe mixture was stirred at 50° C. for 2 hr
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was partitioned with ethyl acetate, 1N aqueous sodium hydroxide solution and aqueous sodium bicarbonate
  6. dry with materialthe organic layer was dried over sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customThe residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=7:3→1:0)
  9. addition4N Hydrochloride-ethyl acetate solution (1 ml) was added to the obtained yellow oil
  10. filtrationthe precipitated crystals were collected by filtration
  11. customrecrystallized

Sources & evidence

ORD record
ord-403c44613ba84c83ac1033e1c8a869f2
Source dataset
uspto-grants-2011_07
Patent number
US07985863B2

Reaction notes

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