Potassium Carbonate → HCID 66970039, compound

HRID 447872Notes

Reaction equation

HRID 447872 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.[NH2:16][CH2:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[NH:25][S:26]([CH3:29])(=[O:28])=[O:27].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:16]([CH2:17][C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=2[NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5417922-Cyano-2-(3,4-dichloro-5(2H)-oxo-2-furyl)acetamideHCID 66876948HCID 66876948, compound

Product 1

HCID 66970039HCID 66970039, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

(Step 3) A suspension of 2-cyano-2-(3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)acetamide (0.77 g), N-[2-(aminomethyl)-4-fluorophenyl]methanesulfonamide hydrochloride obtained in Step 2 (1.0 g) and potassium carbonate (1.36 g) in ethanol (15 ml) was stirred overnight at 70° C. The reaction solution was filtered through celite, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=7:3→1:0). The obtained residue was dissolved in methanol, 4N hydrogen chloride-ethyl acetate solution (1 ml) was added, and the mixture was crystallized from methanol-ethyl acetate. The precipitated crystals were collected by filtration, and recrystallized from methanol-ethyl acetate to give the title compound (0.04 g).

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=7:3→1:0)
  4. dissolutionThe obtained residue was dissolved in methanol
  5. addition4N hydrogen chloride-ethyl acetate solution (1 ml) was added
  6. customthe mixture was crystallized from methanol-ethyl acetate
  7. filtrationThe precipitated crystals were collected by filtration
  8. customrecrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-228846dc0c354d298c020bffc4afd40f
Source dataset
uspto-grants-2013_07
Patent number
US08481569B2

Reaction notes

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