Dimethylformamide → HCID 178520782, compound

Participants

Reaction Steps

To a suspension of 1-phenyl-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7-ium chloride (0.184 g, 0.57 mmol) in dichloromethane (15 mL) was added Hunig's Base (0.45 mL, 2.56 mmol). The mixture was vortexed to ensure dissolution of the reagents followed by the addition of 2-chloro-2-phenylacetyl chloride (0.103 mL, 0.64 mmol). Dimethylformamide (6 mL) and 2-chloro-2-phenylacetyl chloride (15 μL, 0.093 mmol)) was then added and the reaction stirred for another 30 minute at room temperature. On completion of the reaction, water (30 mL) were added and the aqueous layer extracted with EtOAc (50 mL). The organic layer was separated, washed with brine (2×10 mL), dried (Na2SO4), filtered and concentrated under reduced pressure to give the crude product. The crude product was purified using flash column chromatography (SiO2, gradient from 60% EtOAc in hexane to 66% EtOAc in hexane) to give the pure desired product, 2-chloro-2-phenyl-1-(1-phenyl-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)ethanone as an off-white solid (0.120 g, 52%). 1H NMR (400 MHz, DMSO-d6) δ 13.72 (s, 1H), 8.40/8.25 (s, 1H, rotamers), 7.47 (m, 10H), 6.48 (s, 1H), 4.88 (m, 2H), 3.66 (m, 2H), 2.68 and 2.34 (m, 2H, rotamers); LCMS [M+H]: 403.

Provenance & Evidence