Trifluoroacetic acid → 2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-10-(1-isopropylpiperidin-4-ylsulfinyl)-9-methyl-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine

Participants

Reaction Conditions

Reaction Steps

To an ice-cooled solution of 2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-9-(1-isopropylpiperidin-4-ylsulfanyl)-8-methyl-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene from Example 32 (112 mg, 0.233 mmol) in DCM (10 mL) was added TFA (90 μL, 1.165 mmol) followed by a solution of m-CPBA (44 mg, 0.256 mmol) in DCM (2 mL). The resulting mixture was stirred for 20 min at 0° C. then volatiles were removed under reduced pressure. The crude material was purified by column chromatography (C18, gradient 20-50% 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 225 as a white solid (100 mg, 87%). LCMS: RT 2.60 min [M+H]+ 497.1. 1H NMR (DMSO, 400 MHz): δ 8.72 (1H, s), 7.89 (1H, s), 7.00 (1H, s), 5.72-5.60 (1H, m), 4.62-4-47 (4H, m), 2.80 (2H, t, J=11.82 Hz), 2.72-2.57 (2H, m), 2.33 (3H, s), 2.25 (3H, s), 2.18-2.00 (2H, m), 1.81 (1H, bd, J=12.17 Hz), 1.63-1.38 (9H, m), 0.89 (6H, d, J=6.54 Hz)

Provenance & Evidence