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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 512978Generated: October 25, 2026

Cyclohexene → N-[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]-4-amino-2-[tetrahydro-2H-pyran-4-yl(trifluoroacetyl)amino]benzamide

https://huagongshe.com/reaction/512978

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCyclohexeneHCID 8079—
ReactantN-[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]-4-nitro-2-[tetrahydro-2H-pyran-4-yl(trifluoroacetyl)amino]benzamideHCID 86647627—
CatalystPalladiumHCID 23938—
Solvent1,4-DioxaneHCID 31275—
ProductN-[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]-4-amino-2-[tetrahydro-2H-pyran-4-yl(trifluoroacetyl)amino]benzamideHCID 8664762882%

Reaction Conditions

Temperature100 °C

Reaction Steps

A mixture of N-[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]-4-nitro-2-[tetrahydro-2H-pyran-4-yl(trifluoroacetyl)amino]benzamide (3.86 g, 6.4 mmol), cyclohexene (10 mL), dioxane (70 mL) and 10% Pd/C (0.42 g) was stirred at 100° C. for 4 hours. The reaction mixture was filtered over a celite pad washing thoroughly with THF and MeOH. After evaporation of the organic phase, purification of the crude by chromatography over silica gel (DCM/EtOH 9/1) gave 2.75 g of title compound (82% yield).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09102662B2
Source datasetuspto-grants-2015_08
ORD IDord-81c2bf587aea4e6e84516bdab721ca45
Source noteuspto-grants-2015_08