Acetyl chloride → HCID 56598362, compound

Participants

Reaction Steps

To a solution of crude N-(3-fluoro-4-(2-methylpyridin-4-yl)benzyl)-6-(piperazin-1-yl)nicotinamide 20-3 (10 mg, 0.025 mmol) and DIEA (21.8 μL, 0.125 mmol) in dichloromethane (1.0 mL) was added acetyl chloride (3.6 μL, 0.05 mmol), and the solution was stirred 30 minutes at room temperature. The solution was diluted with ethyl acetate (30 mL) and washed with 10% Na2CO3 aqueous solution and water. After the organic phase was dried over Na2SO4, the solvent was evaporated under reduced pressure and the residue subjected to preparative reverse phase HPLC to give 6-(4-acetylpiperazin-1-yl)-N-(3-fluoro-4-(2-methylpyridin-4-yl)benzyl)nicotinamide 20 as a solid. MS m/z 448.2 (M+1). 1H NMR 400 MHz (CDCl3) δ 8.63 (d, 1H), 8.54 (d, 1H), 7.98 (dd, 1H), 7.42 (dd, 1H), 7.33 (bs, 1H), 7.29-7.25 (m, 1H), 7.22 (dd, 1H), 7.16 (dd, 1H), 6.64 (d, 1H), 6.61 (t, 1H), 4.67 (d, 2H), 3.78-3.70 (m, 4H), 3.65-3.54 (m, 4H), 2.61 (s, 3H), 2.14 (s, 3H).

Provenance & Evidence