Triethylamine → N-(3-tert-butylphenyl)-4-oxo-1H-quinoline-3-carboxamide
Reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=[C:3]1[C:12]([OH:14])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.[C:46]([C:50]1[CH:51]=[C:52]([CH:54]=[CH:55][CH:56]=1)[NH2:53])([CH3:49])([CH3:48])[CH3:47]>CN(C=O)C>[C:46]([C:50]1[CH:51]=[C:52]([NH:53][C:12]([C:3]2[C:2](=[O:1])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[NH:5][CH:4]=2)=[O:14])[CH:54]=[CH:55][CH:56]=1)([CH3:49])([CH3:47])[CH3:48]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A flask charged with 4-oxo-1H-quinoline-3-carboxylic acid (38 mg, 0.20 mmol), HBTU (76 mg, 0.20 mmol), Et3N (61 mg, 84 μL, 0.60 mmol) and DMF (2 mL) was heated at 60° C. for 15 minutes. To the reaction mixture was then added 3-tert-butylaniline (29.98 mg, 0.2009 mmol) and the reaction mixture was stirred at 60° C. for an additional 30 minutes. The reaction mixture was cooled to room temperature, filtered and purified via reverse phase HPLC using 10 to 99% CH3CN in H2O to obtain N-(3-tert-butylphenyl)-4-oxo-1H-quinoline-3-carboxamide. 1H NMR (400 MHz, DMSO-d6) δ 12.94 (s, 1H), 12.45 (s, 1H), 8.89 (s, 1H), 8.34 (dd, J=1.1, 8.2 Hz, 1H), 7.84-7.80 (m, 1H), 7.76-7.71 (m, 2H), 7.62-7.53 (m, 2H), 7.29 (t, J=7.9 Hz, 1H), 7.15-7.12 (m, 1H), 1.31 (s, 9H). LC/MS: m/z 321.5 (M+H)+ at 1.8 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).
Workup
- temperatureThe reaction mixture was cooled to room temperature
- filtrationfiltered
- custompurified via reverse phase
Sources & evidence
- ORD record
- ord-7a4c96ad756940a284db40f53b53ae7a
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08614327B2
Reaction notes
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