Nitrogen → (S)-7'-azido-4'-fluoro-2'-methoxy-5,6-dihydrospiro[[1,3]thiazine-4,9'-xanthen]-2-amine

Participants

Reaction Conditions

Reaction Steps

To a disposable vial was charged with (S)-7′-bromo-4′-fluoro-2′-methoxy-5,6-dihydrospiro[[1,3]thiazine-4,9′-xanthen]-2-amine (300 mg, 0.733 mmol), copper(I) iodide (27.9 mg, 0.147 mmol), sodium azide (143 mg, 2.199 mmol) and (+)-sodium 1-ascorbate (14.52 mg, 0.073 mmol). EtOH (1.2 mL) and water (0.5 mL) were added followed by addition of trans-N,N′-dimethyl-1,2-cyclohexanediamine (34.7 μl, 0.220 mmol). The vial was capped and subjected to three cycles of evacuation-backfilling with N2. Finally it was heated in oil bath at 90° C. for 3 hrs. The reaction mixture was allowed to cool to RT. Excess of water was added and a tan precipitate formed. It was collected through Buchner funnel to yield (S)-7′-azido-4′-fluoro-2′-methoxy-5,6-dihydrospiro[[1,3]thiazine-4,9′-xanthen]-2-amine (170 mg, 0.458 mmol, 62.4% yield) as tan solid.

Provenance & Evidence