4-Methylmorpholine → HCID 66775523, compound

Participants

Reaction Steps

A mixture of EXAMPLE 74B (1.3 g), 2-(ethylamino)ethanol (0.363 g), 1-ethyl-3-(3-(dimethylamino)propyl)-carbodiimide hydrochloride (0.78 g), 1-hydroxybenzotriazole hydrate (0.623 g), and N-methylmorpholine (0.748 g) in 5 mL DMF was stirred at room temperature for 10 hours. The reaction mixture was extracted with ethyl acetate 3 times and the combined extracts were washed (brine), dried (MgSO4) and concentrated. The residue was purified by flash chromatography with 0-4% methanol/CH2Cl2 to afford 3-(8-(1H-benzo(d)(1,2,3)triazol-1-yloxy)-1-iodoimidazo[1,5-a]pyrazin-3-yl)-N-ethyl-N-(2-hydroxyethyl)propanamide. MS (ESI(+)) m/e 522 (M+H)+ This product was placed in a high pressure tube with 7N ammonia (15 ml) in methanol, heated at 60 C overnight then concentrated to dryness. The residue was purified by flash column with 0-10% methanol/CH2Cl2 to give the title compound. MS (ESI(+)) m/e 404 (M+H)+

Provenance & Evidence