Diisopropylethylamine → HCID 44554652, compound

Participants

Reaction Steps

A mixture of 2-(1-(3,4-difluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)isonicotinic acid (0.22 g, 0.66 mmol), diisopropylethylamine (0.6 mL, 9.57 mmol), 1-hydroxybenzotriazole monohydrate (0.20 g, 1.44 mmol) and O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.40 g, 1.24 mmol) and (5-methylisoxazol-3-yl)methanamine (0.19 g, 0.99 mmol) in tetrahydrofuran (10 mL) was stirred at ambient temperature for 23 hours and concentrated in vacuo. The residue was suspended in a mixture of saturated sodium bicarbonate solution (10 mL) and ether (2.5 mL) and stirred at ambient temperature overnight. The solid was collected by filtration, washed with saturated sodium bicarbonate solution, water, ether, hexanes and dried in vacuo to afford 2-(1-(3,4-difluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-N-((5-methylisoxazol-3-yl)methyl)-isonicotinamide as a colorless solid (0.20 g, 71% yield): mp 160-161° C.; 1H NMR (300 MHz, CDCl3) δ 8.62 (s, 1H), 8.53 (d, J=5.7 Hz, 1H), 8.46 (s, 1H), 7.70 (dd, J=5.1, 1.4 Hz, 1H), 7.25-7.09 (m, 4H), 6.03 (s, 1H), 4.96 (s, 2H), 4.67 (d, J=5.7 Hz, 2H), 2.41 (s, 3H); MS (ES+) m/z 427.0 (M+1).

Provenance & Evidence