Diisopropylethylamine → HCID 57904985, Verbindung

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.

1. extractionextracted with ethyl acetate
2. customSolids precipitated out of the biphasic mixture
3. filtrationwere collected by filtration

ORD-Eintrag

ord-4bcc2083f7694133a1c2cf8a797f6dac

Quelldatensatz

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08129398B2