Hydrochloric Acid → HCID 178464318, compound

Participants

Reaction Steps

70 mg of 1,1-diethyl-3-[3-[5-fluoro-6-(3-piperidin-1-ylpropoxy)-1H-benzimidazol-2-yl]-1-(tetrahydropyran-2-yl)-1H-pyrazol-4-yl]urea are suspended in 3 mL of a 3N solution of HCl in dioxane. The medium is stirred at ambient temperature for 48 hours. The solvent is evaporated off under vacuum in a rotary evaporator. The reaction crude is purified by flash chromatography on a 4 g silica cartridge, eluent: 100/0 to 80/20 dichloromethane/methanol. The fractions containing the expected product are concentrated and the solid obtained is triturated in isopropyl ether. After filtration and rinsing of the solid, 26.2 mg of 1,1-diethyl-3-{3-[5-fluoro-6-(3-piperidin-1-ylpropoxy)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl}urea hydrochloride are isolated in the form of a sand-colored solid. 1H NMR (400 MHz, DMSO-d6, δ in ppm) after addition of a drop of TFA-d1 (CF3COOD-d1): 1.15 (t, J=7.0 Hz, 6H); 1.39 (m, 1H); from 1.57 to 1.76 (m, 3H); 1.83 (m, 2H); 2.22 (m, 2H); 2.93 (m, 2H); 3.25 (m, 2H); 3.37 (q, J=7.0 Hz, 4H); 3.51 (m, 2H); 4.21 (t, J=6.0 Hz, 2H); 7.34 (d, J=7.5 Hz, 1H); 7.56 (d, J=11.0 Hz, 1H); 8.00 (s, 1H).

Provenance & Evidence