1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 6-Fluoro-pyridine-2-carboxylic acid isobutyl-(8-propyl[1,2,4]triazolo-[1,5-c]pyrimidin-7-ylmethyl)-amide

Participants

Reaction Steps

To a stirred solution of isobutyl-(8-propyl-[1,2,4]triazolo[1,5-c]pyrimidin-7-ylmethyl)-amine (2.8 mmol) and 6-fluoro-pyridine-2-carboxylic acid (0.47g, 3.34 mmol) in DCM (10 ml) is added EDCI (0.61 g) and DMAP (0.153 g). The mixture is stirred at room temperature overnight. DCM (10 ml) is added to dilute the mixture. The mixture is washed with water (5 mL), dried (Na2SO4) and solvent evaporated. Preparative TLC purification of the residue (2:1 of hexane: ethyl acetate) provides the title product. H1 NMR δ (CDCl3) (mixture of rotamers) 9.25 (s, 0.51), 9.18 (s, 0.5H), 8.39 (s, 0.5H), 8.36 (s, 0.5H), 7.78-7.93 (m, 1H), 7.68 (d, 0.5H), 7.57 (d, 0.5H), 6.99 (d, 0.5H), 6.92 (d, 0.5H), 5.03 (s, 1H), 4.89 (s, 1H), 3.52 (d, 1H), 3.35 (d, 1H), 3.12 (t, 1H), 2.83 (t, 1H), 1.95-2.20 (m, 1H), 1.59-1.85 (m, 2H), 0.88-1.10 (m, 6H), 0.82 (t, 3H).

Provenance & Evidence