Trifluoroacetic acid → 6-(Piperidin-4-yl)-[1,2,4]triazolo[4,3-a]pyridine

HRID 1487887Notes

Reaction equation

HRID 1487887 reaction equation
[N:1]1[N:2]=[CH:3][N:4]2[CH:9]=[C:8]([CH:10]3[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]3)[CH:7]=[CH:6][C:5]=12.C(O)(C(F)(F)F)=O>ClCCl>[NH:13]1[CH2:12][CH2:11][CH:10]([C:8]2[CH:7]=[CH:6][C:5]3[N:4]([CH:3]=[N:2][N:1]=3)[CH:9]=2)[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90033778tert-Butyl 4-([1,2,4]triazolo[4,3-a]pyridin-6-yl)piperidine-1-carboxylate2×

Product 1

HCID 596274706-(Piperidin-4-yl)-[1,2,4]triazolo[4,3-a]pyridineYield 749.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-Butyl 4-([1,2,4]triazolo[4,3-a]pyridin-6-yl)piperidine-1-carboxylate (compound 36.1, 0.05 g, 0.165 mmol) in dichloromethane (2 mL) was added TFA (0.2 mL). The mixture was stirred at room temperature for 3 hours. The solvents were removed under reduced pressure. The residue was purified by prep-TLC (10% MeOH in dichloromethane+˜0.5% NH4OH) to give 0.25 g (76%) of the title compound as a light brown oil. m/z (ES+) 203 (M+H)+.

Workup

  1. customThe solvents were removed under reduced pressure
  2. customThe residue was purified by prep-TLC (10% MeOH in dichloromethane+˜0.5% NH4OH)

Sources & evidence

ORD record
ord-abeb98eda7004b6bb5aa4c70e3f87258
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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