HCID 136374763, compound → HCID 178522443, compound

Participants

Reaction Steps

A solution of 130 mg of piperidine-1-carboxylic acid [3-[6-fluoro-5-(4-piperidin-1-ylbutoxy)-1H-benzimidazol-2-yl]-1-(tetrahydropyran-2-yl)-1H-pyrazol-4-yl]amide in 2 mL of dichloromethane and 500 μL of trifluoroacetic acid are stirred for 72 hours at ambient temperature. After evaporation of the solvent under vacuum in a rotary evaporator, the reaction crude is purified by flash chromatography on an Analogix RS-12 cartridge with an eluent of 100% dichloromethane to 90/10 dichloromethane/methanol. 86 mg of N-{3-[6-fluoro-5-(4-piperidin-1-ylbutoxy)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl}piperidine-1-carboxamide in the form of a trifluoroacetate salt are obtained in the form of a yellow solid. 1H NMR (300 MHz, DMSO-d6, δ in ppm): for this batch, we observe a 60%-40% resolution of tautomers with: from 1.20 to 1.94 (broad m, 16H); from 2.70 to 3.43 (m partially masked, 6H); 3.50 (m, 4H); 4.11 (m, 2H); 7.11 (d, J=7.5 Hz, 0.6H); 7.27 (d, J=11.0 Hz, 0.4H); 7.37 (d, J=7.5 Hz, 0.4H); 7.51 (d, J=11.0 Hz, 0.6H); 8.01 (broad s, 1H); 8.94 (broad m, 1H); 9.83 (s, 0.4H); 9.87 (s, 0.6H); 12.95 (s, 0.4H); 13.0 (s, 0.6H); 13.05 (s, 1H).

Provenance & Evidence