Methyl {3-(4-chlorophenyl)-5-oxo-4-[(1E)-3,3,3-trifluoroprop-1-en-1-yl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetate → Methyl [3-(4-chlorophenyl)-5-oxo-4-(3,3,3-trifluoropropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetate

HRID 220690Notes

Reaction equation

HRID 220690 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12](/[CH:13]=[CH:14]/[C:15]([F:18])([F:17])[F:16])[C:11](=[O:19])[N:10]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[N:9]=2)=[CH:4][CH:3]=1>[Pt].CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][CH2:14][C:15]([F:18])([F:16])[F:17])[C:11](=[O:19])[N:10]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 59536880Methyl {3-(4-chlorophenyl)-5-oxo-4-[(1E)-3,3,3-trifluoroprop-1-en-1-yl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetate

Product 1

HCID 59536769Methyl [3-(4-chlorophenyl)-5-oxo-4-(3,3,3-trifluoropropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetate

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

Of the compound from Example 76A, 1.2 g (3.32 mmol), 150 mg of platinum on carbon (5%) and 150 ml of methanol were hydrogenated under standard hydrogen pressure. For work-up, the catalyst was filtered off and the filtrate was concentrated on a rotary evaporator. The crude product was purified by preparative HPLC (Method 20). The product fractions were combined and freed from the solvent on a rotary evaporator. Drying in an HV gave 890 mg (73% of theory) of the title compound.

Workup

  1. filtrationFor work-up, the catalyst was filtered off
  2. concentrationthe filtrate was concentrated on a rotary evaporator
  3. customThe crude product was purified by preparative HPLC (Method 20)
  4. customfreed from the solvent on a rotary evaporator
  5. customDrying in an HV

Sources & evidence

ORD record
ord-1f1c822ea24243898bfbc895009fd50b
Source dataset
uspto-grants-2012_06
Patent number
US08202895B2

Reaction notes

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