Dimethylformamide → HCID 86686554, compound

HRID 1528064Notes

Reaction equation

HRID 1528064 reaction equation
[F:1][C:2]1[C:6]([F:7])=[CH:5][N:4]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17](=[O:22])[C:16]([C:23]4[N:27]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[N:26]=[CH:25][CH:24]=4)=[N:15]3)=[C:10]([OH:34])[CH:9]=2)[CH:3]=1.Cl[C:36]([F:41])([F:40])C([O-])=O.[Na+].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[F:40][CH:36]([F:41])[O:34][C:10]1[CH:9]=[C:8]([N:4]2[CH:5]=[C:6]([F:7])[C:2]([F:1])=[CH:3]2)[CH:13]=[CH:12][C:11]=1[N:14]1[CH:19]=[C:18]([O:20][CH3:21])[C:17](=[O:22])[C:16]([C:23]2[N:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:26]=[CH:25][CH:24]=2)=[N:15]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2734985Sodium chlorodifluoroacetateHCID 68014668HCID 68014668, compound

Product 1

HCID 86686554HCID 86686554, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 1-[4-(3,4-difluoro-1H-pyrrol-1-yl)-2-hydroxyphenyl]-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one (231 mg), sodium chlorodifluoroacetate (152 mg), potassium carbonate (104 mg), DMF (2.5 mL) and water (0.5 mL) was heated under reflux overnight. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate), and crystallized from hexane/ethyl acetate to give the title compound (193 mg).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate)
  8. customcrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-e9d2f8b6d77f402db83e1c7574b7aa96
Source dataset
uspto-grants-2015_07
Patent number
US09090586B2

Reaction notes

Loading…