Trifluoroacetic acid → HCID 178464314, compound

Participants

Reaction Conditions

Reaction Steps

0.7 mL of trifluoroacetic acid is added to a solution of 250 mg of 1,1-diethyl-3-[3-[5-fluoro-6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1-(tetrahydro-pyran-2-yl)-1H-pyrazol-4-yl]urea in solution in 2 mL of dichloromethane. The reaction medium is stirred at 22° C. for 72 hours. The reaction medium is concentrated under vacuum in a rotary evaporator. After evaporation, the reaction crude is purified by flash chromatography on an Intelliflash apparatus on an Analogix RS-12 cartridge. The elution is carried out in pure dichloromethane for 15 min and then in dichloromethane containing 10% of ammoniacal methanol. 100 mg of 1,1-diethyl-3-{3-[5-fluoro-6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl}urea are obtained in the form of a beige solid. 1H NMR (300 MHz, DMSO-d6, δ in ppm): 1.18 (t, J=7.0 Hz, 6H); 2.90 (s, 3H); 3.05 (m, 2H); 3.28 (m, 2H); 3.38 (q, J=7.0 Hz, 4H); 3.54 (m, 4H); 7.24 (d, J=8.0 Hz, 1H); 7.46 (d, J=11.5 Hz, 1H); 8.00 (s, 1H). EI mass spectrum: m/z=414 (M)+.; m/z=341 (M−C4H11N)+; m/z=114 CF3CO2H+. relative to TFA; m/z=72 C4H10N+; m/z=69 CF3+ relative to TFA; m/z=45 CO2H+ relative to TFA, base peak; m/z=43 C2H5N+.

Provenance & Evidence