Trifluoroacetic acid → 2-{5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazin-3-yl}pyridine

HRID 1889038Notes

Reaction equation

HRID 1889038 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]2[CH2:12][CH2:13][N:14](C(OC(C)(C)C)=O)[CH2:15][C:10]2=[N:9][N:8]=1.C(O)(C(F)(F)F)=O>ClCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]2[CH2:12][CH2:13][NH:14][CH2:15][C:10]2=[N:9][N:8]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66599726HCID 66599726, compound

Product 1

HCID 523636372-{5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazin-3-yl}pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl 3-(2-pyridinyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate (I100)(115 mg, 0.382 mmol) in dichloromethane (DCM) (1 mL), TFA (0.588 mL, 7.63 mmol) was added and mixture was stirred at RT for 3 h. Volatiles removed under reduced pressure and residue purified by SCX cartridge eluting first with MeOH and then with 2.0N NH3 in MeOH. Ammonia fractions were concentrated under reduced pressure yielding desired product as a pale yellow solid.60 mg.

Workup

  1. customVolatiles removed under reduced pressure and residue
  2. custompurified by SCX cartridge
  3. washeluting first with MeOH
  4. concentrationAmmonia fractions were concentrated under reduced pressure

Sources & evidence

ORD record
ord-b2666e4431d2480f8349376ab343d907
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

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