Trifluoroacetic acid → 3-Chloro-4-{[3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]methyl}benzoic acid

HRID 536546Notes

Reaction equation

HRID 536546 reaction equation
C([O:5][C:6](=[O:31])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[C:18](=[O:19])[N:17]([CH:20]3[CH2:22][CH2:21]3)[C:16]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)=[N:15]2)=[C:9]([Cl:30])[CH:8]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:30][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][C:10]=1[CH2:13][N:14]1[C:18](=[O:19])[N:17]([CH:20]2[CH2:22][CH2:21]2)[C:16]([C:23]2[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=2)=[N:15]1)[C:6]([OH:31])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58460119tert-Butyl-3-chloro-4-{[3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]methyl}benzoate

Product 1

HCID 584601203-Chloro-4-{[3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]methyl}benzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An amount of 1.38 g (3.00 mmol) of the compound from Example 26A was dissolved in 10 ml of dichloromethane and admixed at RT with 3.0 ml (39 mmol) of trifluoroacetic acid and stirred at RT for 72 h. The mixture was concentrated under reduced pressure and admixed with 10 ml of toluene and concentrated again. This procedure was repeated a further two times. The residue which remained was freed from remnants of solvent under a high vacuum. This gave 1.27 g (63% of theory) of the target compound with a purity of 60%.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. concentrationconcentrated again

Sources & evidence

ORD record
ord-33b0938a1d144cd4bf258c2f4d6b00b9
Source dataset
uspto-grants-2014_10
Patent number
US08859601B2

Reaction notes

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