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

Participants

Role	Name	HCID	Charge
Reactant	Cyclohexene	HCID 8079	—
Reactant	N-[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]-4-nitro-2-[tetrahydro-2H-pyran-4-yl(trifluoroacetyl)amino]benzamide	HCID 86647627	—
Catalyst	Palladium	HCID 23938	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	N-[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]-4-amino-2-[tetrahydro-2H-pyran-4-yl(trifluoroacetyl)amino]benzamide	HCID 86647628	82%

Reaction Conditions

Temperature	100 °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

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09255087B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-1fc7c377914948e0b0c5fd15313ffeb5
Source note	uspto-grants-2016_02