Pyrazole → HCID 21071012, compound

HRID 270855Notes

Reaction equation

HRID 270855 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:13][C:14]([N:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH2:18][CH2:17]1)=[O:15]>CN(C=O)C>[F:28][C:25]1[CH:24]=[CH:23][C:22]([N:19]2[CH2:18][CH2:17][N:16]([C:14](=[O:15])[CH2:13][N:1]3[CH:5]=[CH:4][CH:3]=[N:2]3)[CH2:21][CH2:20]2)=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 18485111-(Chloroacetyl)-4-(4-fluorophenyl)piperazine

Product 1

HCID 21071012HCID 21071012, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Pyrazole (112.33 mg, 1.65 mmol) was dissolved in DMF (10 mL). K2CO3 (228.05 mg, 1.65 mmol) and 2-Chloro-1-[4-(4-fluoro-phenyl)-piperazin-1-yl]-ethanone (300 mg, 1.67 mmol) were added to it. The reaction was heated to 80° C. for 14 h. After completion, the reaction was cooled to room temperature, quenched with brine and then extracted with ethyl acetate. The organic layer was further washed with water (2×25 mL) and brine (2×25 mL) and dried over magnesium sulfate. The solvent was removed by rotary evaporation to give the crude product which was purified by column chromatography on silica gel using a solvent mixture (hexane/ethyl acetate=1/1) to afford the title compound as white solid. 1H NMR (400 MHz, CDCl3): 7.2-7.58 (d, 2H), 6.94-7.2 (t, 2H), 6.84-6.9 (dd, 2H), 6.32-6.36 (t, 1H), 5.6 (s, 2H), 3.76-3.82 (m, 2H), 3.68-3.74 (m, 2H), 3.04-3.1 (m, 2H), 3.0-3.04 (m, 2H). 13C NMR (400 MHz, CDCl3):165, 158, 146.5, 140, 130, 118.4, 118.2, 116, 115.8, 107, 54, 51, 50.8 45.8, 42.8.

Workup

  1. temperatureAfter completion, the reaction was cooled to room temperature
  2. customquenched with brine
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was further washed with water (2×25 mL) and brine (2×25 mL)
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed by rotary evaporation
  7. customto give the crude product which
  8. customwas purified by column chromatography on silica gel using a solvent mixture (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-279b0adb30e64fb7bfa2e9860276299d
Source dataset
uspto-grants-2008_11
Patent number
US07449576B1

Reaction notes

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