Trifluoroacetic acid → HCID 71117564, compound

HRID 2368520Notes

Reaction equation

HRID 2368520 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][N:10]=[C:9]2[NH:17]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:17][C:9]1[N:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71117398HCID 71117398, compound

Product 1

HCID 71117564HCID 71117564, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 1-(4-fluorophenyl)-2-(tritylamino)-1H-imidazole-5-carboxylate (66) (200 mg, 0.419 mmol) in dichloromethane (10 mL) was added trifluoroacetic acid (5 mL). The reaction was stirred at room temperature overnight, concentrated and the residue was dissolved in ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, brine, dried over sodium sulfate, filtered, and concentrated and in vacuo to afford methyl 2-amino-1-(4-fluorophenyl)-1H-imidazole-5-carboxylate (67) as a yellow solid.

Workup

  1. concentrationconcentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe organic layer was washed with saturated sodium bicarbonate, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated and in vacuo

Sources & evidence

ORD record
ord-41f2cb3624f648018d91c8f7096e4104
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

Loading…