Water → HCID 11438196, compound

HRID 2056635Notes

Reaction equation

HRID 2056635 reaction equation
[CH2:1](Br)[CH2:2][CH:3]([CH3:5])[CH3:4].COCCOC[C:13]1[C:26]2[NH:27][N:28]=[C:24]3[C:25]=2[C:16]([C:17](=[O:30])[C:18]2[C:23]3=[CH:22][CH:21]=[CH:20][C:19]=2[OH:29])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:4][CH:3]([CH3:5])[CH2:2][CH2:1][O:29][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]2[C:18]=1[C:17](=[O:30])[C:16]1[C:25]3[C:24]2=[N:28][NH:27][C:26]=3[CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78911-Bromo-3-methylbutaneHCID 11430Potassium CarbonateHCID 178496200HCID 178496200, compound

Product 1

HCID 11438196HCID 11438196, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Isopentyl bromide is added to a mixture of 3-(2-methoxyethoxymethyl)-7-hydroxyanthra[1,9cd]pyrazol-6(2H)-one and potassium carbonate in dimethylformamide at room temperature. After stirring the mixture for sixteen hours, water is added, and the mixture was extracted with ethyl acetate (×2). The combined organic layer is washed with aqueous sodium bicarbonate, water, 1 N hydrochloric acid, and brine, dried and evaporated. The residue is taken in 6N hydrochloric acid and heated at 80° C. for 4 hours. After cooling, the mixture is extracted with ethyl acetate (×2), and the combined organic layer is washed with brine, dried, and evaporated. The residue is purified by column chromatography to afford the title compound as yellow solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (×2)
  2. washThe combined organic layer is washed with aqueous sodium bicarbonate, water, 1 N hydrochloric acid, and brine
  3. customdried
  4. customevaporated
  5. temperatureAfter cooling
  6. extractionthe mixture is extracted with ethyl acetate (×2)
  7. washthe combined organic layer is washed with brine
  8. customdried
  9. customevaporated
  10. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-6dc534c801f843a6a04c892930c2984b
Source dataset
uspto-grants-2008_02
Patent number
US07335676B2

Reaction notes

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