Dimethylamine → HCID 10295563, compound

Participants

Reaction Steps

Mesyl chloride (349 μl, 4.5 mmol) was added to a stirred suspension of 2-{4-[3-(5-methylisoxazol-3-yl)-[1,2,4]triazolo[3,4-α]phthalazin-6-yloxymethyl]-[1,2,3]triazol-1-yl}ethanol (354 mg, 0.9 mmol) in Et3N (629 μl, 4.5 mmol) and CH2Cl2 (50 ml) at 0° C. under N2. The reaction was stirred overnight slowly warming to room temperature. H2O (20 ml) was added and the organics separated, dried and concentrated under reduced pressure. The crude residue was taken up in DMF (5 ml) in a sealed tube and a solution of Me2NH (8 mmol) in THF (2.0 M, 4 ml) was added. The reaction was heated at 80° C. for 4 h. The reaction mixture was concentrated under reduced pressure and then taken up in MeOH/CH2Cl2 and dry loaded onto silica. The mixture was purified by column chromatography on silica using 1.5% MeOH/CH2Cl2 containing 1% NH3 as eluent to yield the desired phthalazine (30 mg, 8%). 1H NMR (360 MHz, CDCl3) δ 8:85 (1H, s), 8.64 (1H, d, J=7.4 Hz), 8.24 (1H, d, J=7.4 Hz), 7.93 (1H, t, J=7.4 Hz), 7.80 (1H, t, J=7.4 Hz), 6.90 (1H, s), 5.77 (2H, s), 4.46 (2H, t, J=6.5 Hz), 2.92 (2H, t, J=6.5 Hz), 2.60 (3H, s), 2.24 (6H, s). m/z (ES+) 420 (M+H+).

Provenance & Evidence