Dichloromethane → 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-(1,2,4)triazolo(4,3-a)pyrazine

HRID 1245379Notes

Reaction equation

HRID 1245379 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[N:7]2[CH:8]=[CH:9][N:10]=[CH:11][C:6]2=[N:5][N:4]=1.ClCCl>[Pd].C(O)C>[F:12][C:2]([F:1])([F:13])[C:3]1[N:7]2[CH2:8][CH2:9][NH:10][CH2:11][C:6]2=[N:5][N:4]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 299234623-(Trifluoromethyl)-1,2,4-triazolo(4,3-a)pyrazine

Product 1

HCID 101764893-(Trifluoromethyl)-5,6,7,8-tetrahydro-(1,2,4)triazolo(4,3-a)pyrazineYield 89.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-(Trifluoromethyl)-1,2,4-triazolo[4,3-α]pyrazine (540 mg, 2.87 mmol, from Step A) was hydrogenated under atmospheric hydrogen with 10% Pd/C (200 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. Dichloromethane was added to the above oil and the insoluble black precipitate was filtered off. Concentration of the filtrate gave the title compound as an oil (495 mg). 1H NMR (500 MHz, CDCl3) δ 2.21 (br, 1H), 3.29 (t, 2H, J=5.5 Hz), 4.09 (t, 2H, J=5.5 Hz), 4.24 (s, 2H). LC/MS (M+1) 193.

Workup

  1. filtrationFiltration through Celite
  2. concentrationfollowed by concentration
  3. customgave a dark colored oil
  4. filtrationthe insoluble black precipitate was filtered off

Sources & evidence

ORD record
ord-ceed90d4c91c4d838d852b3b6cb80165
Source dataset
uspto-grants-2006_10
Patent number
US07125873B2

Reaction notes

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