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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 467954Generated: October 25, 2026

1-Hydroxybenzotriazole → N-(Tetrahydro-2H-pyran-4-yl)-N-[3-(trifluoromethoxy)benzyl]imidazo[1,2-a]pyridine-2-carboxamide

https://huagongshe.com/reaction/467954

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1-HydroxybenzotriazoleHCID 75771—
ReactantImidazo[1,2-a]pyridine-2-carboxylic acidHCID 2062168—
Reactant1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2723939—
ReactantN-[3-(Trifluoromethoxy)benzyl]tetrahydro-2H-pyran-4-amineHCID 58049381—
SolventDimethylformamideHCID 6228—
SolventTriethylamineHCID 8471—
ProductN-(Tetrahydro-2H-pyran-4-yl)-N-[3-(trifluoromethoxy)benzyl]imidazo[1,2-a]pyridine-2-carboxamideHCID 5804937077.6%

Reaction Steps

N-[3-(Trifluoromethoxy)benzyl]tetrahydro-2H-pyran-4-amine (242 mg), imidazo[1,2-a]pyridine-2-carboxylic acid (194 mg), EDC.HCl (199 mg), HOBt (138 mg), dimethylformamide (5 mL) and triethylamine (0.33 mL) was stirred overnight at room temperature. The solvents were distilled off under reduced pressure and following extraction with ethyl acetate, the extract was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline, and dried over anhydrous magnesium sulfate. The desiccant was filtered off and, thereafter, the solvents were concentrated. The residue was purified by column chromatography (NH silica gel cartridge; ethyl acetate) to give the titled compound (286 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08623898B2
Source datasetuspto-grants-2014_01
ORD IDord-475c298679004f1aad31a27ea279918a
Source noteuspto-grants-2014_01