4-Nitro-1-(oxan-2-yl)-1H-pyrazole-3-carbaldehyde → HCID 178452212, compound

Participants

Reaction Conditions

Reaction Steps

0.9 g of 4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazole-3-carbaldehyde is added to a solution of 1.2 g of 4-(4,5-diamino-2-fluorophenyl)piperazine-1-carboxylic acid tert-butyl ester in 30 mL of methanol. The reaction medium is stirred at 22° C. for 16 hours. After evaporation, the reaction crude is purified by flash chromatography, elution being carried out with a mixture of dichloromethane/acetone. 530 mg of 4-{6-fluoro-2-[4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-3H-benzimidazol-5-yl}piperazine-1-carboxylic acid tert-butyl ester are isolated in the form of a red foam. 1H NMR (400 MHz, DMSO-d6, δ in ppm): from 1.35 to 2.25 (m, 6H); 1.43 (s, 9H); 3.03 (m, 4H); 3.52 (m, 4H); 3.72 (m, 1H); 4.00 (m, 1H); 5.65 (dd, J=2.0 and 10.0 Hz, 1H); 7.31 (d, J=8.0 Hz, 1H); 7.54 (d, J=12.0 Hz, 1H); 9.17 (s, 1H). ES mass spectrum: m/z=516 MH+ (base peak).

Provenance & Evidence