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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 490908Generated: October 29, 2026

Dimethylformamide → N'-(Cyclobutylcarbonyl)-1-ethyl(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridine-5-carbohydrazide

https://huagongshe.com/reaction/490908

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantCyclobutanecarboxylic acidHCID 19494—
ReactantDiisopropylethylamineHCID 81531—
ReactantO-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2733207—
Reactant1-Ethyl-4-((tetrahydro-2H-pyran-4-yl)amino)-1H-pyrazolo[3,4-b]pyridine-5-carbohydrazide dihydrochlorideHCID 53487828—
ProductN'-(Cyclobutylcarbonyl)-1-ethyl(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridine-5-carbohydrazideHCID 69067427—

Reaction Conditions

Temperature20 °C

Reaction Steps

TBTU (0.050 g, 0.15 mmol) and diisopropylethylamine (0.04 ml, 0.26 mmol) in DMF (0.5 ml) was added to cyclobutylcarboxylic acid (RYCOOH, 0.015 g, 0.15 mmol). The reaction mixture was stirred for 40 minutes at 20° C. A mixture of Intermediate 19 (0.045 g, 0.13 mmol) and diisopropylethylamine (0.04 ml, 0.26 mmol) in DMF (0.5 ml) was added and the reaction mixture stirred for 18 h. The solvent was removed in vacuo and the residue applied to a SPE cartridge (aminopropyl, 2 g). The cartridge was eluted with methanol to afford Intermediate 65 (0.052 g). LCMS showed MH+=387; TRET=2.28 min.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07528148B2
Source datasetuspto-grants-2009_05
ORD IDord-fd88d79a964d457d9816ed394ea7e3fa
Source noteuspto-grants-2009_05