Water → Benzyl 1-benzyl-2-oxo-6-phenyl-1,2,3,4-tetrahydro-1,7-naphthyridin-3-ylcarbamate

Temperatur

50 °C

To a solution of 3F (400 mg, 1.07 mmol) in DMF (8 mL) was added cesium carbonate (873 mg, 2.68 mmol), followed by benzyl bromide (0.38 mL, 3.21 mmol). The reaction mixture was stirred at 50° C. for 1 h. After cooling to RT, water (100 mL) was added. The reaction mixture was extracted with EtOAc (3×30 mL). During the extraction, some precipitates formed. The solid was collected by filtration and washed with EtOAc to give the title compound (250 mg). The combined organics were washed with saturated NaCl, dried over Na2SO4, filtered and concentrated. The resultant residue was purified by silica gel (40 g) column chromatography eluting with a gradient of EtOAc (0-60%) in hexane to give additional 160 mg of the title compound (total 410 mg, 83%) as a white solid. LC/MS (method A): retention time=3.55 min, (M+H)+=464.

1. temperatureAfter cooling to RT
2. extractionThe reaction mixture was extracted with EtOAc (3×30 mL)
3. extractionDuring the extraction
4. customsome precipitates formed
5. filtrationThe solid was collected by filtration
6. washwashed with EtOAc

ORD-Eintrag

ord-da5066a45f6e4ed9b5bd758502073685

Quelldatensatz

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07368458B2