p-Toluenesulfonic acid → 1-{13-methyl-4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-12-yl}ethan-1-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 12-(1-ethoxyethenyl)-13-methyl-4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaene (160 mg, 0.440 mmol) and p-toluenesulfonic acid (7.5 mg, 0.044 mmol) in acetone (10 mL) was stirred at 60° C. for 75 min. The solid was filtered off and the filtrate was concentrated. The residue was purified by reverse phase Combiflash eluting with a 0-40% gradient of CH3CN in 0.3% NH4HCO3 to afford 1-{13-methyl-4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-12-yl}ethan-1-one (120 mg, 81% yield). LCMS (ESI) m/z: 352.2 [M+H+].

Provenance & Evidence