To a slurry of 0.3 g (0.634 mmol) of 4-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-tetrahydro-pyran-3-carboxylic acid methyl ester (Example 24, Step 1) and potassium carbonate (0.176 g, 1.27 mmol) in DMF (10 mL) was added iodomethane (0.109 g, 0.765 mmol). The reaction was heated at 40° C. for 2 h and then the reaction was allowed to cool to 25° C. over 19 h. The DMF was removed in vacuo and the resulting oil was diluted with ethyl acetate (100 mL) and then washed with water (2×30 mL) and saturated aqueous sodium chloride (30 mL). The organic layer was dried over MgSO4, filtered and concentrated to obtain a crude oil (0.170 g,). The crude product was purified by Biotage Flash 40S chromatography, eluting with 1:1 ethyl acetate:hexanes, to afford 4-{methyl-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonyl]-amino}-tetrahydro-pyran-3-carboxylic acid methyl ester as an amorphous white solid (0.210 g, 68%). MS: 485 (M+H)+.
