Sodium Hydroxide → 4-(4-oxo-1-(tetrahydro-2H-pyran-4-yl)-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxylic acid

HRID 2206018Notes

Reaction equation

[O:1]=[C:2]1[C:7]2[C:8]([C:17]3[CH:18]=[C:19]([C:22]([O:24]C)=[O:23])[S:20][CH:21]=3)=[N:9][N:10]([CH:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[C:6]=2[CH:5]=[CH:4][NH:3]1.[OH-].[Na+]>CO>[O:1]=[C:2]1[C:7]2[C:8]([C:17]3[CH:18]=[C:19]([C:22]([OH:24])=[O:23])[S:20][CH:21]=3)=[N:9][N:10]([CH:11]3[CH2:12][CH2:13][O:14][CH2:15][CH2:16]3)[C:6]=2[CH:5]=[CH:4][NH:3]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of methyl 4-(4-oxo-1-(tetrahydro-2H-pyran-4-yl)-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxylate (125 mg) obtained in Example 21 in methanol (20 mL) was added 1N aqueous sodium hydroxide solution (5 mL) under ice-cooling, and the mixture was stirred at 50° C. for 6 hr. The reaction mixture was concentrated under reduced pressure to evaporate the methanol, and the residue was partitioned between ethyl acetate and 1N hydrochloric acid (6 mL). The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound (119 mg).

Workup

temperaturecooling
concentrationThe reaction mixture was concentrated under reduced pressure
customto evaporate the methanol
customthe residue was partitioned between ethyl acetate and 1N hydrochloric acid (6 mL)
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-45468782c95d468292899ffdfef794d2
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371320B2

Reaction notes

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