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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1526051Generated: October 26, 2026

Diisopropylethylamine → 6-chloro-N-[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]-2-(tetrahydro-2H-pyran-4-ylamino)pyridine-3-carboxamide

https://huagongshe.com/reaction/1526051

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
Reactant4-AminotetrahydropyranHCID 419223—
Reactant2,6-dichloro-N-[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]pyridine-3-carboxamideHCID 86647630—
SolventEthyl AcetateHCID 8857—
Solvent1,4-DioxaneHCID 31275—
Product6-chloro-N-[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]-2-(tetrahydro-2H-pyran-4-ylamino)pyridine-3-carboxamideHCID 86647631—

Reaction Steps

A solution of 2,6-dichloro-N-[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]pyridine-3-carboxamide (80 mg, 0.18 mmol) in dioxane (1 mL) was heated at 100° C. for 24 hours in the presence of DIPEA (0.1 mL, 0.55 mmol) and tetrahydro-2H-pyran-4-amine. (28 mg, 0.28 mmol) Reaction mixture was diluted with EtOAc and washed with water. The organic layer was dried over sodium sulfate, filtered and evaporated. The crude was purified by flash chromatography on silica gel using DCM/EtOH 95:5 as the eluant, affording 57 mg of the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09085558B2
Source datasetuspto-grants-2015_07
ORD IDord-d66f8e33fc4b49c0a8f0d432995d028d
Source noteuspto-grants-2015_07