Potassium Carbonate → HCID 86701834, compound

HRID 1406024Notes

Reaction equation

HRID 1406024 reaction equation
C([CH:3]1[C:12]2[C:11]([C:13]([N:15]([O:17][CH3:18])[CH3:16])=[O:14])=[N:10][N:9]([CH3:19])[C:8]=2[C:7](=O)/[C:6](=[CH:21]/N(C)C)/[CH2:5][CH2:4]1)C.S(O)(O)(=O)=O.[CH3:30][O:31][C:32](=[NH:34])[NH2:33].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:18][O:17][N:15]([CH3:16])[C:13]([C:11]1[C:12]2[CH2:3][CH2:4][CH2:5][C:6]3[C:7](=[N:34][C:32]([O:31][CH3:30])=[N:33][CH:21]=3)[C:8]=2[N:9]([CH3:19])[N:10]=1)=[O:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 169039Carbamimidic acid, methyl ester, sulfate (1:1)HCID 86701841HCID 86701841, compound

Product 1

HCID 86701834HCID 86701834, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl (7E)-7-[(dimethylamino)methylidene]-N-methoxy-N,1-dimethyl-8-oxo-1,4,5,6,7,8-hexahydrocyclohepta[c]pyrazole-3-carboxamide (1.62 g, 5.3 mmol) in CH3CN (130 ml), O-methylisourea sulphate (5.22 g, 21.2 mmol) and K2CO3 (3 g, 22.2 mmol) were added. The reaction mixture was stirred at reflux for 16 h, then it was filtered to remove salts and the solvent was evaporated. The residue was suspended in DCM and washed with water; the organic phase was dried on Na2SO4, filtered and concentrated. The crude was purified by flash-chromatography in silica gel (hexane/AcOEt:1/1) to afford 1 g (62% yield) of the title compound as a white solid.

Workup

  1. temperatureat reflux for 16 h
  2. filtrationit was filtered
  3. customto remove salts
  4. customthe solvent was evaporated
  5. washwashed with water
  6. customthe organic phase was dried on Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude was purified by flash-chromatography in silica gel (hexane/AcOEt:1/1)

Sources & evidence

ORD record
ord-0f86b1caf1c949d5873082161cbe389a
Source dataset
uspto-grants-2014_12
Patent number
US08916577B2

Reaction notes

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