Methyl benzenesulfonate → 3-(5-(1-(4-cyanophenyl)-1H-pyrazol-5-yl)-6-methyl-2-oxo-1-(3-(trifluoromethyl)phenyl)-1,2-dihydropyridine-3-carboxamido)-N,N,N-trimethylpropan-1-aminium benzene sulfonate

Participants

Reaction Conditions

Reaction Steps

A solution of 5-(1-(4-cyanophenyl)-1H-pyrazol-5-yl)-N-(3-(dimethylamino)propyl)-6-methyl-2-oxo-1-(3-(trifluoromethyl)phenyl)-1,2-dihydropyridine-3-carboxamide (synthesised according to Example 7, step 1) (14.40 g, 26.25 mmol) and methyl benzenesulfonate (3.82 ml, 28.88 mmol) in acetone (127 ml) was heated at 55° C. for 18 h. The solvents were removed by rotary evaporation and the foam-like residue was suspended in a mixture of 2-propanol:ethanol (5:1) (100 mL) and heated to 80° C. and was then stirred at room temperature over night. The precipitate was filtered off, washed twice with a mixture of 2-propanol:ethanol (5:1) (2×20 mL), washed once with heptane (50 mL) and air dried to afford 16.94 g of a white powder. The solid was further dried at 55° C. in vacuum overnight to afford of the title compound (16.75 g, 88%) as an off-white solid; 1H NMR (400 MHz, dmso) δ 1.81 (3H, s), 1.90 (2H, m), 3.01 (9H, s), 3.27 (4H, m), 6.72 (1H, d), 7.30 (3H, m), 7.59 (2H, m), 7.67 (2H, d), 7.71 (1H, d), 7.85 (2H, m), 7.94 (4H, m), 8.04 (1H, s), 9.41 (1H, t); APCI-MS m/z: 563 [M+].

Provenance & Evidence