4-Nitro-1-(oxan-2-yl)-1H-pyrazole-3-carbaldehyde → HCID 178526768, compound

Participants

Reaction Steps

A solution of 248 mg of 4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazole-3-carbaldehyde and 278.9 mg of 4-fluoro-5-(2-piperidin-1-ylethoxy)benzene-1,2-diamine in 12 mL of methanol is stirred at ambient temperature overnight. In order for the reaction to be complete, heating is carried out for a further half an hour at reflux and then overnight at ambient temperature. After concentration under vacuum in a rotary evaporator, 515 mg of 5-fluoro-2-[4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-6-(2-piperidin-1-ylethoxy)-1H-benzimidazoleare isolated in the form of a dark solid. 1H NMR (300 MHz, DMSO-d6, δ in ppm): for this batch, we observe a 60%-40% resolution of tautomers with: from 1.31 to 1.78 (m, 9H); from 1.87 to 2.30 (m, 3H); 2.46 (m partially masked, 4H); 2.72 (t, J=6.0 Hz, 2H); 3.69 (m, 1H); 4.00 (m, 1H); 4.19 (t, J=6.0 Hz, 2H); 5.60 (dd, J=2.0 and 9.0 Hz, 1H); 7.26 (d, J=7.5 Hz, 0.6H); 7.41 (d, J=11.5 Hz, 0.4H); 7.45 (d, J=7.5 Hz, 0.4H); 7.53 (d, J=11.5 Hz, 0.6H); 9.18 (s, 1H); 12.85 (broad m, 1H).

Provenance & Evidence