Potassium Acetate → HCID 67975686, compound

HRID 45790Notes

Reaction equation

HRID 45790 reaction equation
C[N:2](/[CH:4]=[C:5]1\[CH2:6][CH2:7][C:8]2[C:9]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:10][N:11]([CH2:15][CH2:16][OH:17])[C:12]=2[C:13]\1=O)[CH3:3].[C:23]([O-:26])(=O)C.[K+].S(O)(O)(=O)=O.C[NH:34]C(=N)O>CN(C=O)C.C(OCC)(=O)C>[OH:17][CH2:16][CH2:15][N:11]1[C:12]2[C:13]3[N:34]=[C:3]([O:26][CH3:23])[N:2]=[CH:4][C:5]=3[CH2:6][CH2:7][C:8]=2[C:9]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:10]1

Participants

6

Reactant 3

HCID 517044Potassium AcetateHCID 57444081Ethyl 6-((dimethylamino)methylene)-1-(2-hydroxyethyl)-7-oxo-4,5,6,7-tetrahydro-1H-indazole-3-carboxylateHCID 178485200HCID 178485200, compound

Product 1

HCID 67975686HCID 67975686, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of ethyl (6E)-6-[(dimethylamino)methylidene]-1-(2-hydroxyethyl)-7-oxo-4,5,6,7-tetrahydro-1H-indazole-3-carboxylate 15 g (49 mmol) in 50 ml of anhydrous DMF, 14.4 g (147 mmol) of anhydrous potassium acetate and 12.60 g (73.0 mmol) of methylisourea sulfate were added. The reaction was stirred at 100° C. for 16 hours. The mixture was diluted with ethyl acetate, washed with H2O, dried over Na2SO4, filtered and evaporated. The crude was purified by column (ethyl acetate:hexane 1:3) to give the title compound 1.2 g (10%). HRMS (ESI) calcd for C15H18N4O4 [M+H]+ 319.3278 found 319.3256.

Workup

  1. washwashed with H2O
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude was purified by column (ethyl acetate:hexane 1:3)

Sources & evidence

ORD record
ord-de6d9dbe5ac6434880d52067e1e3500f
Source dataset
uspto-grants-2013_09
Patent number
US08541576B2

Reaction notes

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