Chloroacetylchloride (0.323 ml) in 1 ml DCM was added at 0° C. to the suspension of 1-methyl-6-(4-(2-(piperidin-4-yl)ethoxy)-3-(trifluoromethyl)phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile (free base) in THF/DCM (1:1, 40 ml) with DIPEA (1.7 ml). The mixture was stirred at rt for 2 hours, then 10 ml methanol added, followed by 200 ml ethyl acetate. The mixture was washed with water (100 ml), sodium bicarbonate (100 ml), dried, filtered, solvent removed, residue was columned on silica gel using 100:5 DCM/MeOH as eluant to give 0.7 g product as off white solid. 1H NMR (CD3OD) δ: 8.25 (d, 1H), 8.22 (s, 1H), 8.10 (s, 1H), 7.87 (s, 1H), 7.10 (d, 1H), 4.58 (m, 1H), 4.21 (t, 2H), 4.09 (d, 1H), 4.08 (d, 1H), 3.99 (s, 3H), 3.90 (m, 1H), 3.12 (t, 1H), 2.65 (t, 1H), 2.2 (m, 1H), 1.8-2.0 (m, 4H), 1.1-1.4 (m, 2H).
