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

HRID 2091732Notes

Reaction equation

HRID 2091732 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-a]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-45e563ee85cd4c0c96e645f9855a60f1
Source dataset
uspto-grants-2013_05
Patent number
US08440668B2

Reaction notes

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