Diisopropylethylamine → 3-(Benzyloxy)-N-(4-fluoro-2-(4,4,5-trimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)benzyl)-4-oxo-6,7,8,9-tetrahydro-4H-7,10-ethanopyrimido[1,2-a][1,3]diazepine-2-carboxamide

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Reaction Steps

A mixture of 3-(benzyloxy)-4-oxo-6,7,8,9-tetrahydro-4H-7,10-ethanopyrimido[1,2-a][1,3]diazepine-2-carboxylic acid (0.03 g, 0.088 mmol), 1-(4-fluoro-2-(4,4,5-trimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)phenyl)methanamine hydrochloride salt (0.043 g, 0.132 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) (0.100 g, 0.264 mmol), 4-(dimethylamino)pyridine (DMAP) (1.074 mg, 8.79 μmol) and diisopropyl ethylamine (0.077 mL, 0.439 mmol) in DMF (2 mL) was stirred at room temperature for 1 h. The mixture was diluted with ethyl acetate and washed with 0.5 N HCl, water followed by brine. The organic phase was dried (Na2SO4), filtered and concentrated to give the title compound as a crude yellow oil. LCMS (M+H) calcd for C30H36FN6O5S: 611.24; found: 611.33.

Provenance & Evidence