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

HRID 1015815Notes

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].[NH2:15][CH2:16][C:17]1[CH:18]=[C:19]([S:23]([NH:26][CH3:27])(=[O:25])=[O:24])[CH:20]=[CH:21][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>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:15]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([S:23](=[O:25])(=[O:24])[NH:26][CH3:27])[CH:18]=2)[CH:10]=1

Participants

Conditions

Temperature: 70 °C

Procedure

(Step 2) To a suspension of 2-cyano-2-(3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)acetamide (0.28 g) and 3-(aminomethyl)-N-methylbenzenesulfonamide obtained in Step 1 (0.36 g) in ethanol (10 ml) was added potassium carbonate (0.25 g) at room temperature, and the mixture was stirred overnight at 70° C. The reaction solution was filtered through celite. 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 (76 mg).

Workup

filtrationThe reaction solution was filtered through celite
customThe solvent was evaporated under reduced pressure
customThe residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=7:3→1:0)
addition4N Hydrochloride-ethyl acetate solution (1 ml) was added to the obtained yellow oil
filtrationthe precipitated crystals were collected by filtration
customrecrystallized

Sources & evidence

ORD record: ord-258f90978b89411d945da58826c23d00
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07985863B2

Reaction notes

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