Trifluoroacetic acid → (S)-Pyridin-2-yl(4-(trifluoromethyl)phenyl)methanamine bis(2,2,2-trifluoroacetate)

HRID 2370775Notes

Reaction equation

HRID 2370775 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C@@H:7]([NH:18]C(=O)OC(C)(C)C)[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1.[C:26]([OH:32])([C:28]([F:31])([F:30])[F:29])=[O:27]>C(Cl)Cl>[F:29][C:28]([F:31])([F:30])[C:26]([OH:32])=[O:27].[F:29][C:28]([F:31])([F:30])[C:26]([OH:32])=[O:27].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C@H:7]([C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:15])([F:16])[F:17])=[CH:10][CH:9]=1)[NH2:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71164819(S)-tert-butyl(pyridin-2-yl(4-(trifluoromethyl)phenyl)methyl)carbamate

Product 1

HCID 86687956(S)-Pyridin-2-yl(4-(trifluoromethyl)phenyl)methanamine bis(2,2,2-trifluoroacetate)

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl (pyridin-2-yl(4-(trifluoromethyl)phenyl)methyl)carbamate (1.83 g, 5.19 mmol) in DCM (12 mL) was added TFA (3.86 mL, 51.9 mmol). The resulting mixture was then stirred at rt for 1 h. The mixture was then concentrated and dried to give the title compound as a yellow oil which was used without further purification in the amide coupling step.

Workup

  1. concentrationThe mixture was then concentrated
  2. customdried

Sources & evidence

ORD record
ord-465915f4037e45469e68f04c3800aeed
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

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