Ethyl 4-chloroacetoacetate → HCID 86721268, compound

HRID 1750426Notes

Reaction equation

HRID 1750426 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][N:7](C(OC(C)(C)C)=O)[C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)(=[S:3])[NH2:2].Cl[CH2:24][C:25](=O)[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>CCO>[F:15][C:12]1[CH:11]=[CH:10][C:9]([C:8]2[NH:7][N:6]=[CH:5][C:4]=2[C:1]2[S:3][CH:24]=[C:25]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:2]=2)=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 69484Ethyl 4-chloroacetoacetateHCID 86721266HCID 86721266, compound

Product 1

HCID 86721268HCID 86721268, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the mixture (415 mg, 1.29 mmol) obtained in step 6 and ethyl 4-chloroacetoacetate (0.192 mL, 1.42 mmol) in EtOH (3.6 mL) was heated under reflux for 4 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate. The solution was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine and dried, and the solvent was evaporated under reduced pressure. The residue was purified by NH-silica gel column chromatography (solvent gradient; 50→66% ethyl acetate/hexane) to give ethyl {2-[5-(4-fluorophenyl)-1H-pyrazol-4-yl]-1,3-thiazol-4-yl}acetate (294 mg, 69%) was obtained as a colorless oil

Workup

  1. temperatureunder reflux for 4 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe solution was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  5. customdried
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by NH-silica gel column chromatography (solvent gradient; 50→66% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-931aa05bca1949b591631809bca9ab1b
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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