Trifluoroacetic acid → 5-Amino-4-[3-(carboxymethyloxy)benzoyl]-1-(4-fluorophenyl)pyrazole

HRID 489843Notes

Reaction equation

HRID 489843 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:30])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][C:23]([O:25]C(C)(C)C)=[O:24])[CH:16]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[CH:9][C:10]([F:13])=[CH:11][CH:12]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:30])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][C:23]([OH:25])=[O:24])[CH:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 98228865-Amino-4-[3-(tert-butoxycarbonylmethyloxy)benzoyl]-1-(4-fluorophenyl)pyrazole

Product 1

HCID 98849735-Amino-4-[3-(carboxymethyloxy)benzoyl]-1-(4-fluorophenyl)pyrazoleYield 68.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-amino-4-[3-(tert-butoxycarbonylmethyloxy)benzoyl]-1-(4-fluorophenyl)pyrazole (1.0 g, 3.3 mmol) and trifluoroacetic acid (15 ml, 194 mmol) in methylene chloride (15 ml) was stirred overnight at room temperature. The organics were removed in vacuo and the residue was dissolved in toluene. The solution was concentrated and the residue was triturated between ethyl acetate and hexane to give 5-amino-4-[3-(carboxymethyloxy)benzoyl]-1-(4-fluorophenyl)pyrazole (0.8 g) as a solid.

Workup

  1. customThe organics were removed in vacuo
  2. dissolutionthe residue was dissolved in toluene
  3. concentrationThe solution was concentrated
  4. customthe residue was triturated between ethyl acetate and hexane

Sources & evidence

ORD record
ord-89c273954dd84da6b15ee5301da0fa51
Source dataset
uspto-grants-2005_12
Patent number
US06979693B2

Reaction notes

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