Methyl N-(triethylammoniosulfonyl)carbamate → HCID 131724942, compound

Participants

Reaction Steps

Burgess reagent (262 mg, 1.1 mmol) was added to a stirred solution of 1,1-dimethylethyl 4-hydroxy-4-[5-({[3-(5-methylisoxazol-3-yl)[1,2,4]triazolo[3,4-α]phthalazin-6-yl]oxy}methyl)pyridin-2-yl]-1-piperidine carboxylate (307 mg, 0.55 mmol) in 1,2-dichloroethane (20 ml) at room temperature under N2 and the reaction heated at reflux for 90 min. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure while dry loading onto silica. The residue was purified by column chromatography on silica using 2% MeOH/CH2Cl2 containing 1% NH3 to yield the desired phthalazine (296 mg, 99%). 1H NMR (360 MHz, CDCl3) δ 8.86 (1H, s), 8.66 (1H, d, J=8.0 Hz), 8.20 (1H, d, J=8.0 Hz), 8.05-8.00 (1H, m), 7.95 (1H, t, J=8.0 Hz), 7.79 (1H, t, J=8.0 Hz), 7.43 (1H, d, J=8.1 Hz), 6.85 (1H, s), 6.66 (1H, m), 5.67 (2H, s), 4.17-4.11 (2H, m), 3.67-3.58 (2H, m), 2.68-2.60 (2H, m), 2.59 (3H, s), 1.49 (9H, s). m/z (ES+) 540 (M+H+).

Provenance & Evidence