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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2068813Generated: 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/2068813

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 8664763163.6%

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 numberUS08299057B2
Source datasetuspto-grants-2012_10
ORD IDord-590c2cd970ea4f90ae1c1b32af868bee
Source noteuspto-grants-2012_10