To a sealed tube containing 2-(2-amino-3-morpholinoquinolin-6-yl)-3-methylbenzonitrile (0.20 g, 0.581 mmol, prepared as in Example 14, Step 1) was added phenylmagnesium chloride, 2.0M solution in THF (1.16 mL, 2.323 mmol) under N2 atmosphere. The mixture was heated at 60° C. overnight and the conversion was completed, determined by LCMS. The mixture was allowed to cool to RT and treated with aqueous 2N HCl (1 ml) carefully. The resulted mixture was heated at 60° C. for 7 h until the imine was consumed. The product mixture was concentrated and then diluted with MeOH and purified on HPLC (10-100% MeCN/H2O with 0.1% TFA modifier) to afford (2-(2-amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(phenyl)methanone (TFA salt).
