A mixture of 2-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid (28 mg), 5-(1-ethyl-pentyl)-[1,3,4]thiadiazol-2-ylamine (20 mg), O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (30 mg), diisopropylethylamine (0.04 ml) in DMF (1 ml) was shaked in shaker overnight. The mixture was quenched with water, basified with satuated sodium bicarbonate, and extracted twice with ethyl acetate. The organic layer was separated, dried over sodium sulfate, and concentrated to give the crude material. The crude material was purified by biotage silica gel column chromatography using methylene chloride to 3% methanol in methylene chloride to give the title compound as a glass foam. LC-MS RT=2.5 min, M+1=465.0, M−1=463.2. The corresponding HCl salt was prepared as an off-white solid.
