Trifluoroacetic acid → 2-Amino-1-{3-[2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-azetidin-1-yl}-2-methyl-propan-1-one

Participants

Reaction Steps

To a solution of (2-{3-[2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-azetidin-1-yl}-1,1-dimethyl-2-oxo-ethyl)-carbamic acid tert-butyl ester (203 mg, 0.36 mmol) in DCM (2 mL) was added TFA (2 mL) and the reaction mixture was stirred for 1 hour then concentrated in vacuo. The residual solid was triturated with ether, filtered off and air-dried before being dissolved in DCM. The organic solution was washed (aqueous saturated sodium bicarbonate solution, followed by water and then brine), dried (MgSO4) and concentrated in vacuo. The residue was freeze-dried from MeOH/H2O to give 469 as a white solid (116 mg, 71%). LCMS: RT=8.13 min, [M+H]+=453. 1H NMR δ (ppm) (DMSO-d6): 8.30 (1H, d, J=8.19 Hz), 8.06 (1H, s), 7.18 (1H, dd, J=8.24, 1.86 Hz), 7.00 (1H, d, J=1.82 Hz), 5.82-5.74 (1H, m), 4.79 (1H, s), 4.42 (1H, s), 4.33 (2H, t, J=5.13 Hz), 4.19 (1H, s), 3.77-3.70 (2H, m), 3.39 (2H, t, J=5.02 Hz), 1.74 (2H, s), 1.50 (6H, d, J=6.59 Hz), 1.17 (6H, s)

Provenance & Evidence