Trifluoroacetic acid → HCID 69096970, compound

HRID 2409985Notes

Reaction equation

HRID 2409985 reaction equation
[Cl:1][C:2]1[C:3]([O:25][CH3:26])=[CH:4][C:5]([CH2:16][C:17](=O)[C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[C:6]([NH:8]C(=O)OC(C)(C)C)[CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]2[C:5]([CH:16]=[C:17]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[NH:8]2)=[CH:4][C:3]=1[O:25][CH3:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86703302HCID 86703302, compound

Product 1

HCID 69096970HCID 69096970, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl [5-chloro-4-methoxy-2-(2-oxo-2-pyridin-3-ylethyl)phenyl]carbamate (1.28 g) in dichloromethane (17 mL) was added trifluoroacetic acid (3.4 mL) under ice-cooling, and the mixture was stirred at room temperature for 24 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, and the resulting mixture was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine successively. The organic layer was dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain the title compound (812 mg). 1H-NMR (CDCl3) δ ppm: 3.95 (3H, s), 6.77-6.85 (1H, m), 7.14 (1H, s), 7.38 (1H, dd, J=4.8, 8.0 Hz), 7.45 (1H, s), 7.86-7.96 (1H, m), 8.36 (1H, br s), 8.53-8.60 (1H, m), 8.90-8.97 (1H, m).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe resulting mixture was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine successively
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6ba0a3cbfae24f62a19aea2c01494bff
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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