Acetic Anhydride → N-(5-(4-chlorophenyl)-2-{4-[2-(4-methylpiperidin-1-yl)ethoxy]phenylethynyl}pyridin-3-yl)acetamide

Participants

Reaction Steps

125 μL (1.345 mmol) of acetic anhydride was added at RT to a solution of 100 mg (0.224 mmol) of 5-(4-chlorophenyl)-2-{4-[2-(4-methylpiperidin-1-yl)ethoxy]phenylethynyl}pyridin-3-ylamine (Example 19.1d) and 62 μL (0.448 mmol) of triethylamine in 5 mL of DCM and the mixture was refluxed for 72 hours. The reaction mixture was diluted with DCM, and the organic phase was washed with saturated aqueous sodium bicarbonate solution, water, and 12% aqueous HCl, dried over magnesium sulfate, and evaporated down in vacuo. The residue was triturated with DIPE, and the precipitate was filtered off and dried in vacuo. The crude product was purified by HPLC-MS (Zorbax Stable Bond C18, gradient 0.15% formic acid in water/acetonitrile 10/90→90/10 v/v). Yield: 23 mg (21% of theoretical); C29H30ClN3O2 (M=488.020); calc.: molpeak (M+H)+: 488/490 (Cl); found: molpeak (M+H)+: 488/490 (Cl); HPLC-MS: 5.01 minutes (method B).

Provenance & Evidence