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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 564518Generated: October 30, 2026

Hydrochloric Acid → 3-[({[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic Acid

https://huagongshe.com/reaction/564518

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantLithium hydroxide, monohydrateHCID 168937—
ReactantMethyl 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoateHCID 57813262—
SolventMethanol--water (1/1)HCID 22242641—
Product3-[({[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic AcidHCID 5781327771.1%

Reaction Conditions

Temperature80 °C

Reaction Steps

To the solution of methyl 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoate (0.29 g, 0.623 mmol) in MeOH/H2O (2/1 mL) was added LiOH.H2O (0.131 g, 3.12 mmol). The mixture was heated with a microwave at 80° C. for 30 min. Then HCl (1 N) was added to adjust the about pH 4˜5. The solvent was removed. The residue was washed with H2O and a little EtOAc and dried under vacuum to afford the title compound 0.20 g (70%). LC-MS m/z 452 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08067408B2
Source datasetuspto-grants-2011_11
ORD IDord-9d2bc43435a846afaee36c4f06901db7
Source noteuspto-grants-2011_11