Trifluoroacetic acid → HCID 178464312, compound

Participants

Reaction Conditions

Reaction Steps

0.5 mL of trifluoroacetic acid is added to a solution of 39 mg of 1,1-diethyl-3-[3-[5-fluoro-6-(4-methylperhydro-1,4-diazepin-1-yl)-1H-benzimidazol-2-yl]-1-(tetrahydropyran-2-yl)-1H-pyrazol-4-yl}urea in solution in 1 mL of dichloromethane. The reaction medium is stirred at 22° C. for 16 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-4 cartridge. The elution is carried out with pure dichloromethane and then with dichloromethane containing 5% of ammoniacal methanol. 12 mg of 1,1-diethyl-3-{3-[5-fluoro-6-(4-methylperhydro-1,4-diazepin-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl}urea trifluoroacetate salt are obtained in the form of a black resin. 1H NMR (300 MHz, DMSO-d6, δ in ppm): 1.10 (t, J=7.0 Hz, 6H); 2.20 (broad m, 2H); 2.89 (s, 3H); from 3.07 to 3.68 (m, 8H); 3.34 (q, J=7.0 Hz, 4H); 7.22 (d, J=7.5 Hz, 1H); 7.55 (d, J=12.0 Hz, 1H); 7.96 (s, 1H). EI mass spectrum: m/z=428 M+., m/z=355 (M−C4H11N)+, m/z=69 CF3+ (relative to TFA), m/z=58 C3H8N+ (base peak), m/z=45 CO2H+ (relative to TFA).

Provenance & Evidence