Trifluoroacetic acid → 2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-10-(1-isopropylpiperidin-4-ylsulfinyl)-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-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene 176 (410 mg, 0.91 mmol) in DCM (40 mL) was added TFA (210 μL, 2.72 mmol) followed by a solution of m-CPBA (172 mg, 0.997 mmol) in DCM (10 mL). The resulting mixture was stirred for 1 h at 0° C. then washed with a saturated solution of NaHCO3, followed by water, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 0-13% 2M NH3/MeOH in DCM followed by Si-PCC, gradient 0-16% 2M NH3/MeOH in EtOAc and then Si-PCC, gradient 0-10% 2M NH3/MeOH in DCM) affording racemic 177 (181 mg, 43%). LCMS: RT 2.48 min [M+H]+ 469.2. 1H NMR (MeOD, 400 MHz): δ 8.77 (1H, d, J=2.30 Hz), 7.95 (1H, s), 7.82 (1H, s), 7.59 (1H, dd, J=8.59, 2.31 Hz), 7.29 (1H, d, J=8.58 Hz), 5.95-5.87 (1H, m), 4.60 (4H, s), 3.03-2.93 (2H, m), 2.82 (1H, tt, J=11.83, 4.02 Hz), 2.75-2.67 (1H, m), 2.28-2.19 (2H, m), 1.91-1.79 (2H, m), 1.78-1.61 (2H, m), 1.57 (6H, 2d, J=6.63 Hz), 1.03 (6H, d, J=6.56 Hz)

Provenance & Evidence