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To an ice-cooled solution of 9-(1-isopropylpiperidine-4-sulfinyl)-2-(4-methylpyridin-2-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene 223 (86 mg, 0.19 mmol) in DCM (7 mL) was added TFA (74 μL, 0.953 mmol) followed by a slow addition of a solution of m-CPBA (43 mg, 0.248 mmol) in DCM (2 mL) and the resulting mixture was stirred for 3 h at 0° C. Volatiles were removed under reduced pressure and the resulting residue was purified by column chromatography (C18, gradient 5-40% MeOH in 0.5% TFA/H2O) and then loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH and the product eluted with 0.5M NH3 in MeOH. Further column chromatography purification (Si-PCC, gradient 2-8% 2M NH3/MeOH in DCM) afforded 224 as a white solid (69 mg, 77%). LCMS: RT 2.08 min [M+H]+ 467.1. 1H NMR (DMSO, 400 MHz): δ 8.95 (1H, d, J=2.41 Hz), 8.40 (1H, d, J=4.98 Hz), 7.96 (1H, s), 7.80 (1H, s), 7.70 (1H, dd, J=8.62, 2.44 Hz), 7.29 (1H, d, J=8.62 Hz), 7.09 (1H, dd, J=5.05, 1.56 Hz), 4.65-4.55 (4H, m), 3.24-3.15 (1H, m), 2.83 (2H, bd, J=11.14 Hz), 2.70-2.60 (1H, m), 2.41 (3H, s), 2.09 (2H, t, J=11.51 Hz), 1.88 (2H, d, J=12.14 Hz), 1.54-1.41 (2H, m), 0.90 (6H, d, J=6.55 Hz)

1. customVolatiles were removed under reduced pressure
2. customthe resulting residue was purified by column chromatography (C18, gradient 5-40% MeOH in 0.5% TFA/H2O)
3. washThe cartridge was washed with MeOH
4. washthe product eluted with 0.5M NH3 in MeOH
5. customFurther column chromatography purification (Si-PCC, gradient 2-8% 2M NH3/MeOH in DCM)