Water → HCID 178522437, compound

Participants

Reaction Conditions

Reaction Steps

0.5 mL of water is added to a solution of 380 mg of 4-{6-fluoro-2-[4-[(piperidine-1-carbonyl)amino]-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-3H-benzimidazol-5-yl}piperazine-1-carboxylic acid tert-butyl ester in solution in 2 mL of trifluoroacetic acid. The reaction medium is stirred at 22° C. for 48 hours. The reaction medium is concentrated under vacuum in a rotary evaporator. The reaction crude is purified by flash chromatography on an Intelliflash apparatus on an Analogix RS-40 cartridge. The elution is carried out with pure dichloromethane and then with dichloromethane containing 5% of ammoniacal methanol. 195 mg of N-[3-(5-fluoro-6-piperazin-1-yl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-piperidine-1-carboxamide are obtained in the form of a yellow solid. 1H NMR (400 MHz, DMSO-d6, δ in ppm): from 1.48 to 1.68 (m, 6H); 3.23 (m, 4H); 3.30 (m, 4H); 3.47 (m, 4H); 7.24 (d, J=8.0 Hz, 1H); 7.48 (d, J=11.5 Hz, 1H); 8.01 (s, 1H). ES mass spectrum: m/z=413 MH+, m/z=328 (M+H—C5H11N)+, m/z=227.9 (M+CH3CN+2H)2+/2 (base peak). Remark: the acetonitrile explaining the m/z=227.9 peak is in the mobile phase.

Provenance & Evidence