反应详情

To a solution of 9-(1-tert-butylpiperidin-4-ylsulfanyl)-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene, also named as 10-(1-tert-butylpiperidin-4-ylthio)-2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine 139 (280 mg, 0.60 mmol) in DCM (30 mL) at 0° C. was added TFA (139 μL, 1.81 mmol) followed by a solution of m-CPBA (114 mg, 0.66 mmol) in DCM (10 mL). The resulting mixture was stirred for 30 min then washed with a saturated aqueous NaHCO3 solution, dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 0-12% 2M NH3/MeOH in DCM then C18, gradient 10-35% MeOH in H2O) affording racemic 140 as a white solid (227 mg, 78%). LCMS: RT 2.55 min [M+H]+ 483.4. 1H NMR (DMSO, 400 MHz): δ 8.77 (1H, d, J=2.30 Hz), 7.94 (1H, s), 7.81 (1H, s), 7.58 (1H, dd, J=8.59, 2.31 Hz), 7.29 (1H, d, J=8.58 Hz), 5.89-5.88 (1H, m), 4.59 (4H, s), 3.18 (2H, s), 2.23 (2H, s), 1.91 (1H, s), 1.87 (2H, s), 1.69-1.64 (2H, m), 1.56 (6H, dd, J=6.63, 3.37 Hz), 1.07 (9H, s)

1. washthen washed with a saturated aqueous NaHCO3 solution
2. dry with materialdried (Na2SO4)
3. concentrationconcentrated in vacuo
4. customThe resulting residue was purified by column chromatography (Si-PCC, gradient 0-12% 2M NH3/MeOH in DCM