Hydrochloric Acid → HCID 66968414, compound

HRID 1366985Notes

Reaction equation

HRID 1366985 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[CH:9][NH:8][N:7]=1)=[O:5])[CH3:2].[H-].[Na+].[CH:20]([N:23]([CH2:27]C)[CH:24](C)C)(C)[CH3:21].ClCCN(C)C.Cl>CN(C=O)C.[I-].[K+].O>[CH2:1]([O:3][C:4]([CH:6]1[C:10]([C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)=[CH:9][NH:8][N:7]1[CH2:21][CH2:20][N:23]([CH3:27])[CH3:24])=[O:5])[CH3:2]

Participants

9

Reactant 5

HCID 313Hydrochloric Acid2×HCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 81531DiisopropylethylamineHCID 178470488HCID 178470488, compound

Product 1

HCID 66968414HCID 66968414, compoundYield 29.3%

Reagents, catalysts & solvents 3

HCID 4875Potassium IodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-(4-Fluoro-phenyl)-1H-pyrazole-3-carboxylic acid ethyl ester (2.4 g, 10 mmol) was added to an ice-cooled slurry of sodium hydride (0.82 g, 60% dispersion in mineral oil, 20 mmol) in DMF (20 ml), under argon. N,N-diisopropylethylamine (1.8 ml, 10 mmol) was added followed by 2-chloro-ethyl dimethylamine.HCl (1.48 g, 10 mmol) and potassium iodide (5 mg). The reaction mixture was stirred at room temperature for 16 h then at 80° C. for 48 h. 2N HCl and water were added and the product extracted with ethyl acetate (3×). The combined organics were washed with brine, dried (Na2SO4) and the solvent removed in vacuo. Chromatography (silica gel, 3-10% methanol-dichloromethane) afforded 2-(2-dimethylamino-ethyl)-4-(4-fluoro-phenyl)-1H-pyrazole-3-carboxylic acid ethyl ester (900 mg) and the title compound (630 mg).

Workup

  1. waitat 80° C. for 48 h
  2. extractionthe product extracted with ethyl acetate (3×)
  3. washThe combined organics were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-d73c836e648248cb836b71c4289d318a
Source dataset
uspto-grants-2011_02
Patent number
US07893090B2

Reaction notes

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