Dimethylamine, hydrochloride → (S)-ethyl 2-tert-butoxy-2-(5-(4-chlorophenyl)-2-(dimethylcarbamoyl)-7-methylquinolin-6-yl)acetate

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To a stirred solution of (S)-6-(1-tert-butoxy-2-ethoxy-2-oxoethyl)-5-(4-chlorophenyl)-7-methylquinoline-2-carboxylic acid (14 mg, 0.032 mmol), dimethylamine HCl salt (13 mg, 0.16 mmol) and DIPEA (0.056 mL, 0.32 mmol) in DMF (1 mL) was added HATU (61 mg, 0.16 mmol) at 0° C. The mixture was stirred for 2 hours at ambient temperature. The mixture was diluted with ethyl acetate (30 mL) and washed with water and brine, then dried over Na2SO4. Concentration and purification by column chromatography provided the product (7 mg, 45%). LCMS-ESI+ (m/z): 483.2, 485.3 (M+H)+.

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