4-Nitro-1-(oxan-2-yl)-1H-pyrazole-3-carbaldehyde → HCID 178526766, compound

Participants

Reaction Conditions

Reaction Steps

3 g of 4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazole-3-carbaldehyde and 43 mg of ferric chloride are added to a solution of 3 g of 4-fluoro-5-perhydro-1,4-oxazepin-4-ylbenzene-1,2-diamine in 60 mL of DMF. The reaction medium is stirred at 22° C. for 16 hours. After evaporation, the reaction crude is purified by flash chromatography. The elution is carried out in a 1/1 mixture of cyclohexane/ethyl acetate. 3 g of 5-fluoro-2-[4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-6-perhydro-1,4-oxazepin-4-yl-1H-benzimidazoleare isolated in the form of a red oil. 1H NMR (400 MHz, DMSO-d6, δ in ppm): from 1.40 to 2.25 (m, 8H); from 3.25 to 3.39 (m partially masked, 4H); 3.70 (m, 1H); 3.78 (m, 4H); 3.99 (m, 1H); 5.59 (dd, J=2.5 and 9.5 Hz, 1H); 7.16 (broad m, 1H); 7.39 (broad d, J=11.5 Hz, 1H); 9.17 (s, 1H); 12.75 (broad m, 1H).

Provenance & Evidence