4-Nitro-1-(oxan-2-yl)-1H-pyrazole-3-carbaldehyde → HCID 178483560, compound

Participants

Reaction Conditions

Reaction Steps

3.4 g of 4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazole-3-carbaldehyde are added to a solution of 3.5 g of 4-(3-dimethylaminopropoxy)-5-fluorobenzene-1,2-diamine in 150 mL of methanol. The reaction medium is stirred at 22° C. for 18 hours. After evaporation, the reaction crude is purified by flash chromatography on an Intelliflash apparatus on an Analogix RS-330 cartridge. The elution is carried out in dichloromethane with 10% of methanol. 2.3 g of (3-{6-fluoro-2-[4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-3H-benzimidazol-5-yloxy}-propyl)dimethylamine are isolated. 1H NMR (300 MHz, DMSO-d6, δ in ppm): 1.50 to 2.23 (m, 8H); 2.80 (s, 6H); 3.23 (m, 2H); 3.68 (m, 1H); 3.98 (m, 1H); 4.17 (t, J=6.0 Hz, 2H); 5.58 (dd, J=2.5 and 9.5 Hz, 1H); 7.34 (d, J=8.0 Hz, 1H); 7.49 (d, J=11.0 Hz, 1H) 9.11 (s, 1H).

Provenance & Evidence