Ethyl Acetate → 5,6,7,8-Tetrahydro-2-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrazine

HRID 1454799Notes

Reaction equation

HRID 1454799 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[N:11]=[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][N:5]2[N:4]=1.C(OCC)(=O)C.CO.ClCCl>[Pd].C(O)C>[F:12][C:2]([F:1])([F:13])[C:3]1[N:11]=[C:6]2[CH2:7][NH:8][CH2:9][CH2:10][N:5]2[N:4]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 21226129Dichloromethane methanolHCID 533933572-(Trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrazine

Product 1

HCID 341763295,6,7,8-Tetrahydro-2-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrazine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-(Trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrazine (340 mg, 1.81 mmol, from Step C) was hydrogenated under atmospheric hydrogen with 10% palladium on carbon (60 mg) as a catalyst in ethanol (10 mL) at ambient temperature for 18 h. Filtration through Celite followed by concentration gave a dark colored oil. Flash chromatography (100% ethyl acetate, then 10% methanol/dichloromethane) gave the title compound as a white solid. 1H-NMR (500 MHz, CDCl3): δ 1.80 (br, 1H), 3.40 (t, 2H, J=5.5 Hz), 4.22-4.26 (m, 4H); LC/MS 193 (M+1).

Workup

  1. filtrationFiltration through Celite
  2. concentrationfollowed by concentration
  3. customgave a dark colored oil

Sources & evidence

ORD record
ord-10c812d188e84d03956c5b2778ed4268
Source dataset
uspto-grants-2009_01
Patent number
US07482336B2

Reaction notes

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