Sodium Cyanide → N-benzyl-2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-isonicotinamide

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Reaction Steps

A solution of methyl 2-(3-(3,4-difluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate (0.25 g, 0.72 mmol) and sodium cyanide (0.10 g, 2.04 mmol) in pyridin-2-ylmethanamine (3.0 mL) was stirred at 95° C. for 16 hours and concentrated in vacuo. The residue was purified by column chromatography eluted with 0 to 90% of ethyl acetate in dichloromethane to give N-benzyl-2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-isonicotinamide as a colorless solid (0.17 g, yield 54%): mp 99-101° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.74 (t, J=6.0 Hz, 1H), 8.62 (s, 1H), 8.49-8.47 (m, 1H), 8.39 (d, J=5.1 Hz, 1H), 7.76-7.70 (m, 1H), 7.44-7.22 (m, 5H), 7.19-7.15 (m, 1H), 4.54 (d, J=6.0 Hz, 2H), 4.39 (s, 2H), 3.96 (t, J=8.1 Hz, 2H), 3.38 (t, J=8.1 Hz, 2H); MS (ES+) m/z 423.8 (M+1).

Provenance & Evidence