1-(3,4-Dichlorophenyl)-4,4,4-trifluorobutane-1,3-dione → 5-(3,4-Dichlorophenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-2-carboxylic acid

HRID 2307939

Reaction equation

HRID 2307939 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=O)[CH2:10][C:11](=O)[C:12]([F:15])([F:14])[F:13])[CH:5]=[CH:6][C:7]=1[Cl:8].[NH2:18][C:19]1[NH:23][N:22]=[C:21]([C:24]([OH:26])=[O:25])[CH:20]=1>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([C:12]([F:15])([F:14])[F:13])[N:23]3[N:22]=[C:21]([C:24]([OH:26])=[O:25])[CH:20]=[C:19]3[N:18]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 124462551-(3,4-Dichlorophenyl)-4,4,4-trifluorobutane-1,3-dioneHCID 178418848HCID 178418848, compound

Product 1

HCID 10836755-(3,4-Dichlorophenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-2-carboxylic acidYield 90.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-(3,4-Dichloro-phenyl)-4,4,4-trifluoro-butane-1,3-dione (1.00 g, 3.51 mmol) and 5-amino-1H-pyrazole-3-carboxylic acid (0.446 g, 3.51 mmoL) in acetic acid (100 mL) was heated at reflux for 48 hours. The reaction concentrated under reduced pressure and the crude product was purified by column chromatography on silica gel to give 5-(3,4-dichloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (1.20 g, 90%).

Workup

  1. temperatureat reflux for 48 hours
  2. concentrationThe reaction concentrated under reduced pressure
  3. customthe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-7ae5b223561f4f959c0061a3fb738854
Source dataset
uspto-grants-2004_12
Patent number
US06833371B2

Linked notes

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