Trifluoroacetic acid → 10-(1-Isopropylpiperidin-4-ylsulfinyl)-2-(4-methylpyridin-2-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine

Participants

Reaction Conditions

Reaction Steps

To an ice-cooled solution of 9-(1-isopropylpiperidin-4-ylsulfanyl)-2-(4-methylpyridin-2-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene from Example 12 (138 mg, 0.317 mmol) in DCM (20 mL) was added TFA (122 μL, 1.59 mmol) followed by a solution of m-CPBA (60 mg, 0.349 mmol) in DCM (2 mL). The resulting mixture was stirred for 15 min at 0° C. then volatiles were removed under reduced pressure. The crude material 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 affording 223 as a colorless foam (114 mg, 80%). LCMS: RT1.94 min [M+H]+ 501.0. 1H NMR (DMSO, 400 MHz): δ 8.70 (1H, d, J=2.27 Hz), 8.38 (1H, d, J=4.97 Hz), 7.92 (1H, s), 7.81 (1H, s), 7.50 (1H, dd, J=8.51, 2.30 Hz), 7.23 (1H, d, J=8.51 Hz), 7.07 (1H, d, J=5.03 Hz), 4.59-4.50 (4H, m), 2.86-2.78 (2H, m), 2.74-2.58 (2H, m), 2.39 (3H, s), 2.15-2.01 (2H, m), 1.76 (1H, bd, J=12.05 Hz), 1.59-1.43 (3H, m), 0.90 (6H, d, J=6.53 Hz)

Provenance & Evidence