Hydrochloric Acid → HCID 87055066, compound

Participants

Reaction Steps

To a solution of 6-bromo-1H-benzo[d][1,3]oxazine-2,4-dione (22 mg, 0.09 mmol) in 1 ml dioxane was added DIEA (31 μl) followed by (S)-1-(4-fluorophenyl)-2-methoxyethanamine (15 mg, 0.09 mmol). The mixture was microwaved at 100° C. for 30 min. Then 250 μl 2N HCl (aq.) was added followed by a solution of NaNO2 (12.4 mg in 250 μl water). The mixture was stirred at RT for 1 h. To this mixture, 0.5 mL EtOAc was added and stirred for 5 min. Then, the stirring was stopped and the layers were allowed to separate. The bottom aqueous layer was removed by a pipette and was then 250 μl 1N K3PO4 (aq.) was added. To this mixture was added 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide (30 mg, 0.06 mmol) followed by Pd(dtbpf)Cl2 (2 mg). The vial was sealed and microwaved at 80° C. for 2 h. The reaction mixtures were diluted with 0.5 mL H2O and the aq. layers were separated. The organic was diluted with 0.5 mL DMF and filtered. The filtrate was purified using semi-prep HPLC to provide (S)-2-(4-fluorophenyl)-5-(3-(1-(4-fluorophenyl)-2-methoxyethyl)-4-oxo-3,4-dihydrobenzo[d][1,2,3]triazin-6-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide. (M+H)+: 674.

Provenance & Evidence