2-Bromopropane → HCID 11742023, compound

HRID 1437289Notes

Reaction equation

HRID 1437289 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:12][C:11]([C:20]([N:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[O:21])=[N:10]2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH:34](Br)([CH3:36])[CH3:35]>CN(C)C=O>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:12][C:11]([C:20]([N:22]3[CH2:27][CH2:26][N:25]([CH:34]([CH3:36])[CH3:35])[CH2:24][CH2:23]3)=[O:21])=[N:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 10451352HCID 10451352, compound

Product 1

HCID 11742023HCID 11742023, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-[1-(6-methoxy-3-pyridyl)-5-phenylpyrazole-3-carbonyl]piperazine (0.446 g) obtained in Example 16 in N,N-dimethylformamide (7.5 mL), potassium carbonate (0.505 g) and isopropyl bromide (0.30 mL) were added at room temperature, and the mixture was stirred at 60° C. for 16 hours, and then cooled in air. The reaction mixture was partitioned between water and ethyl acetate. Subsequently, the aqueous layer was extracted with ethyl acetate. The organic layers were combined and washed with saturated brine, followed by drying over sodium sulfate anhydrate. After filtration, the solvent was removed under reduced pressure. The residue was purified through silica gel column chromatography (chloroform-methanol), to thereby give the title compound as an oily product (0.283 g, 57%).

Workup

  1. temperaturecooled in air
  2. customThe reaction mixture was partitioned between water and ethyl acetate
  3. extractionSubsequently, the aqueous layer was extracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialby drying over sodium sulfate anhydrate
  6. filtrationAfter filtration
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified through silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-59483af9bf9e43abacdffd106f5ba950
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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