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 11880Notes

Reaction equation

HRID 11880 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-7e3cd44aa54b46a5be88c3b168754af2
Source dataset
uspto-grants-2006_08
Patent number
US07098335B2

Reaction notes

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