Diisopropylethylamine → HCID 57904985, compound

Participants

Reaction Steps

A mixture of 10-amino-N-(4-fluorobenzyl)-3-hydroxy-4-oxo-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxamide (0.05 g, 0.122 mmol), 2-((2-fluoroethyl)(methyl)amino)-2-oxoacetic acid (0.036 g, 0.245 mmol), diisopropyl ethylamine (0.128 mL, 0.734 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) (0.093 g, 0.245 mmol) and 4-(dimethylamino)pyridine (DMAP) (2.99 mg, 0.024 mmol) in DMF (1.2 mL) was stirred at room temperature for 16 h. The mixture was diluted with 1N HCl and extracted with ethyl acetate. Solids precipitated out of the biphasic mixture and were collected by filtration to give the title compound as white needles (0.0394 g, 60% yield). 1H NMR (500 MHz, CDCl3) δ: 11.92-12.05 (1 H, m), 8.16-8.68 (2 H, m), 7.28-7.42 (2 H, m), 6.91-7.10 (2 H, m), 4.37-4.75 (4 H, m), 4.16 (2 H, t, J=4.58 Hz), 3.94-4.08 (1 H, m), 3.50-3.65 (1 H, m), 2.91-3.43 (3 H, m), 2.53-2.66 (2 H, m), 2.45-2.52 (1 H, m), 1.88-2.11 (4 H, m), 1.61-1.78 (2 H, m). LCMS (M+H) calcd for C24H28F2N5O5: 504.20; found: 504.02.

Provenance & Evidence