Water → 4-methoxy-3-[4-(4-morpholinyl)phenyl]-1H-Pyrazolo[4,3-c]pyridine

HRID 2206209Notes

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]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:18][CH:17]=2)=[N:6]1)(C)(C)C.O>FC(F)(F)C(O)=O>[CH3:15][O:14][C:9]1[C:8]2[C:7]([C:16]3[CH:17]=[CH:18][C:19]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[CH:20][CH:21]=3)=[N:6][NH:5][C:13]=2[CH:12]=[CH:11][N:10]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 1-tert-butyl-4-methoxy-3-(4-(morpholin-4-yl)phenyl)-1H-pyrazolo[4,3-c]pyridine (2.2 g) in trifluoroacetic acid (50 mL) was added water (5 mL), and the mixture was stirred overnight at 130° C. The reaction mixture was concentrated under reduced pressure. To the obtained residue was added saturated aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.332 g).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
additionTo the obtained residue was added saturated aqueous sodium bicarbonate solution
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-6f40e33b7ecb4105b2db509537492929
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371320B2

Reaction notes

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