2,4,6-Trimethylpyridine → HCID 16073865, compound

Participants

Reaction Steps

Methanesulfonyl chloride (0.10 mL) is added to a cold (0° C.) solution of N-(4-chlorobenzyl)-6-(hydroxymethyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide (0.41 g) from Preparation No. 10, DMAP (0.030 g), and 2,4,6-collidine (0.19 mL) in anhydrous DMF (15 mL). The mixture is stirred at room temperature for 12 h and then benzomorpholine (1.60 g) from above is added. The reaction mixture is stirred at room temperature for 2 h and is then heated to 65° C. overnight. The mixture is cooled to room temperature and poured water. The solid is dissolved in CH2Cl2/MeOH and adsorbed onto silica. Purification by column chromatography (eluent CH2Cl2 (1 L), 1% MeOH/CH2Cl2 (2 L)) and then recrystallization from CH2Cl2/hexanes affords 0.56 g (100%) of the title compound as a pale gold solid.

Provenance & Evidence