4-(1-tert-butyl-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)benzenesulfonamide → 4-(4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)benzenesulfonamide
Reaction equation
C([N:5]1[C:13]2[CH:12]=[CH:11][N:10]=[C:9]([O:14][CH3:15])[C:8]=2[C:7]([C:16]2[CH:21]=[CH:20][C:19]([S:22]([NH2:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)=[N:6]1)(C)(C)C>FC(F)(F)C(O)=O.O>[CH3:15][O:14][C:9]1[C:8]2[C:7]([C:16]3[CH:17]=[CH:18][C:19]([S:22]([NH2:25])(=[O:24])=[O:23])=[CH:20][CH:21]=3)=[N:6][NH:5][C:13]=2[CH:12]=[CH:11][N:10]=1Participants
4
Procedure
4-(1-tert-Butyl-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)benzenesulfonamide (878 mg) obtained in Step D of Example 86 was dissolved in a mixed solvent of trifluoroacetic acid (50 mL)/water (5 mL), and the solution was heated with reflux for 24 hr. The reaction mixture was allowed to be cooled to room temperature, and concentrated under reduced pressure. The residue was extracted with ethyl acetate and saturated aqueous sodium hydrogencarbonate solution, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (561 mg).
Workup
- temperaturethe solution was heated
- temperaturewith reflux for 24 hr
- concentrationconcentrated under reduced pressure
- extractionThe residue was extracted with ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
- washthe organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-3aa1f93e97824747b0f7d2e583517080
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09371320B2
Reaction notes
Loading…