Methanesulfonic Acid → 6-Methoxy-4-(6-methyl-2-thiazol-2-yl-pyridin-3-yloxy)-quinolin-7-ol
Reaction equation
FC(F)(F)C(O)=O.CS(O)(=O)=O.C([O:20][C:21]1[CH:30]=[C:29]2[C:24]([C:25]([O:31][C:32]3[C:33]([C:39]4[S:40][CH:41]=[CH:42][N:43]=4)=[N:34][C:35]([CH3:38])=[CH:36][CH:37]=3)=[CH:26][CH:27]=[N:28]2)=[CH:23][C:22]=1[O:44][CH3:45])C1C=CC=CC=1.C(=O)([O-])O.[Na+]>>[CH3:45][O:44][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][C:21]=1[OH:20])[N:28]=[CH:27][CH:26]=[C:25]2[O:31][C:32]1[C:33]([C:39]2[S:40][CH:41]=[CH:42][N:43]=2)=[N:34][C:35]([CH3:38])=[CH:36][CH:37]=1Participants
Conditions
- Temperature
- 80 °C
Procedure
Trifluoroacetic acid (1 ml) and methanesulfonic acid (0.1 ml) were added to 7-benzyloxy-6-methoxy-4-(6-methyl-2-thiazol-2-yl-pyridin-3-yloxy)-quinoline (compound 328) (40 mg), and the mixture was stirred at 80° C. for 1.5 hr. The reaction solution was cooled to room temperature, and a saturated aqueous sodium hydrogencarbonate solution was then added to the reaction solution. The mixture was made alkaline, and the mixture was then extracted with chloroform. The chloroform layer was washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-methanol to give the title compound (23 mg, yield 70%).
Workup
- temperatureThe reaction solution was cooled to room temperature
- extractionthe mixture was then extracted with chloroform
- washThe chloroform layer was washed with water
- dry with materialwas dried over anhydrous sodium sulfate
- customThe solvent was removed by distillation under the reduced pressure
- customthe residue was purified by thin layer chromatography
Sources & evidence
- ORD record
- ord-9d4d47b277a343e7a631318ed8c396af
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07560558B2
Reaction notes
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