N-methyl-2-pyrrolidone → HCID 53330218, compound

Participants

Reaction Steps

1-Methyl-6-(4-(2-(piperidin-4-yl)ethoxy)-3-(trifluoromethyl)phenyl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile (76 mg), Boc-1-aminocyclopropane-1-carboxylic (71.1 mg) and DIPEA (146 μl) were dissolved in NMP (2 ml) and HATU (0.265 mmol, 101 mg) was then added. The reaction was stirred at room temperature for 72 hours then diluted with EtOAc (20 ml) and washed with 1:1 saturated sodium bicarbonate solution/water (3×15 ml). Organics were dried over sodium sulphate and solvent evaporated under reduced pressure. The resulting residue was re-dissolved in DCM (1 ml) and acetonitrile (200 μl) and trifluoroacetic acid (200 μl) added. The mixture was stirred for 30 minutes at room temperature then solvent evaporated under reduced pressure. Toluene (500 μl) was added and then removed under reduced pressure. The resulting brown residue was purified by flash chromatography (10 g silica column, DCM to 5% MeOH in DCM gradient). Solvent was evaporated under reduced pressure and the resulting solid was washed with DCM and ether and dried under vacuum to afford desired product 6-(4-(2-(1-(1-aminocyclopropanecarbonyl)piperidin-4-yl)ethoxy)-3-(trifluoromethyl)phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile (52% yield) as a solid.

Provenance & Evidence