Dimethylamine → HCID 24953754, compound

Participants

Reaction Steps

To a solution of (R)-6-chloro-N-(2-chloro-5-((1-phenylethylamino)methyl)phenyl)nicotinamide 48 (0.175 g, 0.44 mmol) in THF (3 mL) at 0° C. was added dimethylamine (5.0 mL, 153 mmol). The reaction mixture was warmed to room temperature, stirred for 20 h, quenched with saturated NaHCO3, and diluted with EtOAc. The organic phase was washed with saturated NaHCO3 (1×), brine (1×), dried over MgSO4, filtered, and concentrated in vacuo. Purification by flash column chromatography on silica gel (eluted with 50% to 100% EtOAc in hexanes) gave (R)—N-(2-chloro-5-((1-phenylethylamino)methyl)phenyl)-6-(dimethylamino)nicotinamide 49 (0.118 g, 66% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ 1.37 (d, J=6.5 Hz, 3H), 3.19 (s, 6H), 3.60 (d, J=13.5 Hz, 1H), 3.66 (d, J=13.5 Hz, 1H), 3.81 (q, J=6.6 Hz, 3H), 6.57 (d, J=8.6 Hz, 1H), 7.00 (dd, J=8.2, 2.2 Hz, 1H), 7.25-7.37 (m, 7H), 8.00 (dd, J=9.0, 2.5 Hz, 1H), 8.27 (s, 1H), 8.49 (d, J=2.0 Hz, 1H), 8.76 (d, J=2.2 Hz, 1H). Mass spectrum: calculated for C23H25ClN4O 408.2. found 409.2 (M++1).

Provenance & Evidence