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

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A solution of methyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate (0.26 g, 0.78 mmol) and sodium cyanide (78 mg, 1.56 mmol) in benzylamine (5.0 mL) was stirred at 95° C. for 16 hours and concentrated in vacuo. The residue was purified by column chromatography eluting with 0 to 90% of ethyl acetate in hexanes to give N-benzyl-2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinamide as a colorless solid (0.19 g, yield 59%): mp 167-169° C.; 1H NMR (300 MHz, CDCl3) δ 8.57 (d, J=0.6 Hz, 1H), 8.37 (d, J=5.1 Hz, 1H), 7.42-7.18 (m, 8H), 7.08-6.98 (m, 2H), 6.79 (br s, 1H), 4.62 (d, J=6.0 Hz, 2H), 4.41 (s, 2H), 4.03 (t, J=7.5 Hz, 2H), 3.36 (t, J=7.8 Hz, 2H); 13C NMR (75 MHz, CDCl3) δ 165.7, 164.0, 160.7, 157.0, 153.0, 148.4, 143.0, 137.7, 132.1, 132.0, 129.9, 129.8, 128.8, 128.0, 127.7, 116.1, 115.8, 115.6, 109.0, 47.2, 44.2, 41.3, 41.0; MS (ES+) m/z 405.2 (M+1).

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