Trifluoroacetic acid → 3-Bromo-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine

HRID 523111Notes

Reaction equation

HRID 523111 reaction equation
[Br:1][C:2]1[N:6]2[CH2:7][CH2:8][N:9](C(OC(C)(C)C)=O)[CH2:10][C:5]2=[N:4][N:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[N:6]2[CH2:7][CH2:8][NH:9][CH2:10][C:5]2=[N:4][N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 17998723tert-Butyl 3-bromo-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate

Product 1

HCID 179987223-Bromo-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazineYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate (52 mg, 0.172 mmol) in DCM (6 mL) at 0° C. was added TFA (0.26 mL). The reaction was stirred at room temperature for 16 hours before concentrating in vacuo. The residue was purified by elution through an SCX-2 column using 2M NH3/MeOH to give the title compound as yellow solid (29 mg, 83%).

Workup

  1. concentrationbefore concentrating in vacuo
  2. customThe residue was purified by elution through an SCX-2 column

Sources & evidence

ORD record
ord-a52c156d7eba442bb8f7f0a214e4075a
Source dataset
uspto-grants-2016_05
Patent number
US09334286B2

Reaction notes

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