Trifluoroacetic acid → HCID 68829037, compound
Reaction equation
[NH2:1][C:2]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:8]([CH2:18][NH:19]C(=O)OC(C)(C)C)=[C:7]2[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[F:33])=[O:3].FC(F)(F)C(O)=O>>[NH2:19][CH2:18][C:8]1[C:9]([CH2:14][CH:15]([CH3:17])[CH3:16])=[N:10][C:11]2[C:6]([C:7]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[F:33])=[CH:5][C:4]([C:2]([NH2:1])=[O:3])=[CH:13][CH:12]=2Participants
Procedure
A mixture of tert-butyl [6-(aminocarbonyl)-4-(2-fluorophenyl)-2-isobutylquinolin-3-yl]methylcarbamate (0.32 g, 0.70 mmol) and trifluoroacetic acid (4 ml) was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate-tetrahydrofuran (1:1, 50 ml) and 10% aqueous potassium carbonate solution (50 ml). The organic layer was washed with saturated brine (15 ml) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography. The obtained crude crystals were recrystallized from n-hexane-ethyl acetate to give the title compound (0.15 g, yield 61%) as colorless crystals.
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- customthe residue was partitioned between ethyl acetate-tetrahydrofuran (1:1, 50 ml) and 10% aqueous potassium carbonate solution (50 ml)
- washThe organic layer was washed with saturated brine (15 ml)
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by silica gel column chromatography
- customThe obtained crude crystals
- customwere recrystallized from n-hexane-ethyl acetate
Sources & evidence
- ORD record
- ord-4ba8609e5ddc419dabf05c11426f29cb
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07547710B2
Reaction notes
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