HCID 178418361, compound → HCID 178480423, compound

Participants

Reaction Steps

A suspension of 11.9 g of 5-fluoro-6-(4-methylperhydro-1,4-diazepin-1-yl)-2-[4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-1H-benzimidazole in 260 mL of methanol and 1.2 g of palladium-on-charcoal is hydrogenated under 1 bar of hydrogen pressure at ambient temperature for 18 hours. The reaction medium is filtered through celite and the filtrate is concentrated under reduced pressure in a rotary evaporator. 10.9 g of 3-[5-fluoro-6-(4-methylperhydro-1,4-diazepin-1-yl)-1H-benzimidazol-2-yl]-1-(tetrahydropyran-2-yl)-1H-pyrazol-4-ylamine are obtained in the form of a brown powder. 1H NMR (300 MHz, DMSO-d6, δ in ppm): 1.43 to 2.17 (m, 8H); 2.33 (s, 3H); 2.64 (m, 2H); 2.73 (m, 2H); from 3.20 to 3.40 (m masked, 4H); 3.62 (m, 1H); 3.95 (m, 1H); 4.92 (broad s, 2H); 5.31 (dd, J=2.5 and 10.0 Hz, 1H); from 6.91 to 7.36 (m, 2H); 7.31 (s, 1H); 12.4 (broad m, 1H). ES mass spectrum: m/z=414: MH+ (base peak)—m/z=330: (MH−C5H8O)+

Provenance & Evidence