HCID 86693107, compound → HCID 86693106, compound

Participants

Reaction Steps

In a 25-mL round-bottom flask, a suspension of 9-(1-hydroxy-3-benzoyloxy-cyclobutylethynyl)-8-fluoro-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carboxylic acid amide (190 mg, ˜0.4 mmol), lithiumol (96 mg, 4.01 mmol) in methanol (0.5 mL) and water (1 mL) was stirred at room temperature overnight. The resulting solution was diluted with 20 mL of dichloromethane and 10 mL water. The organic layer was washed with 10 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (1:10). This resulted in 7 mg of 9-(1,3-Dihydroxy-cyclobutylethynyl)-8-fluoro-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carboxylic acid amide as a light yellow solid (single undetermined diasteromer). LC-MS (ES, m/z):358[M+H]+; 1H-NMR (400 MHz, DMSO-d6, ppm) δ: 8.570 (d, 1H), 7.783 (s, 1H), 7.591 (br s, 1H), 7.139 (br s, 1H), 7.015 (d, 1H), 5.982 (s, 1H), 5.200 (d, 1H), 4.520-4.496 (m, 4H), 4.000-3.949 (m, 1H), 2.760-2.716 (m, 2H), 2.164-2.115 (m, 2H).

Provenance & Evidence