Pyrazole → HCID 54055756, compound

HRID 2227480Notes

Reaction equation

HRID 2227480 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][CH2:8][C:9]1[C:14]([CH3:15])=[C:13]([N+:16]([O-:18])=[O:17])[CH:12]=[C:11]([Br:19])[C:10]=1F)([CH3:4])([CH3:3])[CH3:2].[NH:22]1[CH:26]=[CH:25][CH:24]=[N:23]1.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C=O>C(OCC)(=O)C.O>[C:1]([O:5][C:6](=[O:21])[NH:7][CH2:8][C:9]1[C:14]([CH3:15])=[C:13]([N+:16]([O-:18])=[O:17])[CH:12]=[C:11]([Br:19])[C:10]=1[N:22]1[CH:26]=[CH:25][CH:24]=[N:23]1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 1048PyrazoleHCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 53953326HCID 53953326, compound

Product 1

HCID 54055756HCID 54055756, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of the compound (233 mg) obtained in Example 7c, pyrazole (53 mg), sodium carbonate (82 mg) and dimethylformamide (6 ml) was stirred at 100° C. for 2 hours. Water was added to the reaction mixture and extraction with ethyl acetate was conducted. The organic layer was washed with brine, dried with anhydrous magnesium sulfate and then concentrated at reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:3) to give the titled compound (yield, 62%).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried with anhydrous magnesium sulfate
  3. concentrationconcentrated at reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:3)

Sources & evidence

ORD record
ord-d9c27bf7552349d48533a34d7a48e100
Source dataset
uspto-grants-2002_07
Patent number
US06414005B1

Reaction notes

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