Toluene → 1-(6-Fluoro-3,4-dihydro-5-oxa-1,2a-diazaacenaphthylen-2-yl)ethylamine

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Reaction Steps

To an ice-cooled solution of the mixture of [1-(6-fluoro-3,4-dihydro-5-oxa-1,2a-diaza-acenaphthylen-2-yl)ethyl]carbamic acid tert-butyl ester and N-[1-(6-fluoro-3,4-dihydro-5-oxa-1,2a-diaza-acenaphthylen-2-yl)ethyl]acetamide from the previous step in DCM (15 mL) was added TFA (3 mL) and the mixture was stirred at RT for 2 h. Toluene was added and volatiles were removed under reduced pressure, the resulting residue was dissolved in MeOH and loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH and the product was eluted with 0.5M NH3/MeOH. The product containing fractions were combined and concentrated in vacuo. Purification by column chromatography (Si—PCC, gradient 2-8% 2M NH3/MeOH in DCM) afforded the title compound as a light brown gum (185.6 mg, 65%, 2 steps). LCMS (Method B): RT 1.54 min [M+H]+ 222

Provenance & Evidence