Sodium Hypochlorite → HCID 118558158, compound

Participants

Reaction Steps

Sodium hypochlorite (1.408 mL, 0.912 mmol) was added to a stirred, room temperature mixture of (E)-tert-butyl 5-(2-(4-fluorophenyl)-6-((hydroxyimino)methyl)-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate (100 mg, 0.228 mmol) and 6-fluoro-2-(prop-1-en-2-yl)benzo[d]oxazole (40.4 mg, 0.228 mmol) in dichloromethane (2 mL) and the mixture was stirred at room temperature for overnight. The reaction was checked with LCMS and starting material was all consumed. The mixture was diluted with dichloromethane (10 mL), washed with aqueous sodium hydrogen carbonate (saturated, 1×6 mL), dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with EtOAc/isohexane=50% to give tert-butyl 5-(4-chloro-6-(5-(6-fluorobenzo[d]oxazol-2-yl)-5-methyl-4,5-dihydroisoxazol-3-yl)-2-(4-fluorophenyl)-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate (48 mg, 0.074 mmol) as a yellow solid, 648.0 (M+H+); and tert-butyl 5-(6-(5-(6-fluorobenzo[d]oxazol-2-yl)-5-methyl-4,5-dihydroisoxazol-3-yl)-2-(4-fluorophenyl)-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate (26 mg, 0.042 mmol) as a yellow solid which were deprotected with TFA as in Example 5.1 to give Examples 6.1 and 6.2 respectively.

Provenance & Evidence