Trifluoromethanesulfonic anhydride → HCID 90341039, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(11-fluoro-6-(hydroxymethyl)-5,6-dihydroindolo[1,2-h][1,7]naphthyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (180 mg, 0.280 mmol) in DCM (8 mL) at 0° C. was added trifluoromethanesulfonic anhydride in DCM (0.560 mL, 0.560 mmol). The mixture was stirred at 0° C. for 2 h, then at RT for 1 h. The mixture was evaporated in vacuo to remove the volatiles, redissolved in DMF (8 mL), followed by addition of N,N-diisopropyl ethylamine (362 mg, 2.80 mmol) and 3-fluoroazetidine hydrochloride (125 mg, 1.120 mmol). The mixture was heated to 60° C. and stirred for 3 h. 20 ml H2O was added and the mixture stirred for 10 min. Filtration collected the yellow solid. After washing with additional H2O, the yellow solid was purified by chromatography, and eluted with 0-70% ethyl acetate in hexane to gave 5-(11-fluoro-6-((3-fluoroazetidin-1-yl)methyl)-5,6-dihydroindolo[1,2-h][1,7]naphthyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (42 mg, yield: 21%). MS (M+H)+: 700.

Provenance & Evidence