Trifluoroacetic acid → 4-(aminomethyl)-1-(2-(trifluoromethyl)pyridin-4-yl)pyridin-2(1H)-one

HRID 711265Notes

Reaction equation

HRID 711265 reaction equation
[O:1]=[C:2]1[CH:7]=[C:6]([CH2:8][NH:9]C(=O)OC(C)(C)C)[CH:5]=[CH:4][N:3]1[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:9][CH2:8][C:6]1[CH:5]=[CH:4][N:3]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([C:23]([F:26])([F:24])[F:25])[CH:18]=2)[C:2](=[O:1])[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86679722Tert-butyl (2-oxo-1-(2-(trifluoromethyl)pyridin-4-yl)-1,2-dihydropyridin-4-yl)methylcarbamate

Product 1

HCID 672086134-(aminomethyl)-1-(2-(trifluoromethyl)pyridin-4-yl)pyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of tert-butyl (2-oxo-1-(2-(trifluoromethyl)pyridin-4-yl)-1,2-dihydropyridin-4-yl)methylcarbamate 56-6 (95 mg, 0.26 mmol) in DCM (2 mL) was added TFA (2 mL) at room temperature. The reaction was stirred at room temperature for 30 minutes. The solvent and TFA was removed by rotary evaporation to give crude 4-(aminomethyl)-1-(2-(trifluoromethyl)pyridin-4-yl)pyridin-2(1H)-one 56-7. MS m/z 270.2 (M+1).

Workup

  1. customThe solvent and TFA was removed by rotary evaporation

Sources & evidence

ORD record
ord-ada867bbee6241a890a933da014dcd45
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Reaction notes

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