Sodium Cyanide → N-benzyl-2-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)isonicotinamide
Reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[C:11](=[O:12])[N:10]([C:13]3[CH:14]=[C:15]([CH:20]=[CH:21][N:22]=3)[C:16](OC)=[O:17])[CH:9]=[N:8]2)=[CH:4][CH:3]=1.[C-:25]#[N:26].[Na+]>C(N)C1C=CC=CC=1>[CH2:25]([NH:26][C:16](=[O:17])[C:15]1[CH:20]=[CH:21][N:22]=[C:13]([N:10]2[C:11](=[O:12])[N:7]([CH2:6][C:5]3[CH:23]=[CH:24][C:2]([F:1])=[CH:3][CH:4]=3)[N:8]=[CH:9]2)[CH:14]=1)[C:2]1[CH:24]=[CH:23][CH:5]=[CH:4][CH:3]=1Participants
4
Procedure
A solution of methyl 2-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)isonicotinate and sodium cyanide (0.80 g, 1.43 mmol) in benzylamine (50 mL) was stirred at 100° C. for 23 hours and at 110° C. for 3 hours and concentrated in vacuo. The residue was dissolved in ethyl acetate (30 mL), washed with water (20 mL) and brine (20 mL). The organic solution was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo to dryness. The residue was purified by column chromatography eluting with ethyl acetate in dichloromethane (0% to 50%) to give N-benzyl-2-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)isonicotinamide as a colorless solid (0.29 g, 6%): mp 173-175° C.; 1H NMR (300 MHz, CDCl3) δ 8.56-8.55 (m, 1H), 8.49 (dd, J=5.1, 0.6 Hz, 1H), 8.41 (s, 1H), 7.73-7.70 (m, 1H), 7.32-7.22 (m, 7H), 7.00-6.95 (m, 3H), 4.90 (s, 2H), 4.60 (d, J=5.7 Hz, 2H); MS (ES+) m/z 403.9.