4-Nitro-1-(oxan-2-yl)-1H-pyrazole-3-carbaldehyde → HCID 178483736, compound

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Reaction Steps

A solution of 1 g of N4-(2-dimethylaminoethyl)-5-fluorobenzene-1,2,4-triamine in 30 mL of methanol with 1.06 g of 4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazole-3-carbaldehyde is stirred at ambient temperature for 72 hours. After evaporation of the solvent under vacuum in a rotary evaporator, the reaction crude is purified by flash chromatography on an Intelliflash apparatus on an Analogix RS-90 cartridge with an eluent of 100% dichloromethane to 85/15 dichloromethane/methanol. 350 mg of N1-{6-fluoro-2-[4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-3H-benzimidazol-5-yl}-N2,N2-dimethylethane-1,2-diamine are isolated in the form of an orange foam. ES mass spectrum: 418(+)=(M+H)(+); 334(+)=(M+H)(+)-THP+H, 209.6=(M+2H)(2+)

Provenance & Evidence