Water → N-(8-indol-1-yl-octyl)-3,5-bis(3-chlorophenyl)-4-(2-hydroxyethoxy)benzamide

Temperatur

140 °C

To a solution of N-(8-indol-1-yl-octyl)-3,5-bis(3-chlorophenyl)4-hydroxybenzamide (0.205 g, 0.35 mmol) in DMF (2 ml) was added ethylene carbamate (0.039 g, 0.438 mmol) and tetraethylammonium bromide (0.007 g, 0.035 mmol). The reaction mixture was warmed to 140° C. After 2.5 h, the reaction mixture was poured into water (50 ml) and extracted with EtOAc (3×20 ml). The combined organics were washed with water (3×10 ml), brine (2×10 ml), dried over Na2SO4, filtered and the filtrate concentrated in vac and dried. The residue was purified by preparatory plate chromatography (50% EtOAc/Hex) to give the product as a viscous yellow oil (0.185 g, 84%); 1H NMR (300 MHz, DMSO-d6) δ1.25 (broad s, 8H), 1.44-1.55 (m, 2H), 1.65-1.77 (m, 2H), 3.07-3.17 (m, 2H), 3.20-3.30 (m, 4H), 4.14 (t, J=7.5 Hz, 2H), 4.44 (broad s, 1H), 6.38 (d, J=3 Hz, 1H), 6.98 (t, J=7.5 Hz, 1H), 7.09 (t, J=7.5 Hz, 1H), 7.34 (d, J=3 Hz, 1H), 7.40-7.52 (m, 6H), 7.56 7.65 (m, 2H), 7.70 (s, 2H), 7.88 (s, 2H), 8.54 (t, J=4 Hz, 1H); mass spectrum [(+)ESI], m/z 629 (M+H)+.

1. extractionextracted with EtOAc (3×20 ml)
2. washThe combined organics were washed with water (3×10 ml), brine (2×10 ml)
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. concentrationthe filtrate concentrated in vac
6. customdried
7. customThe residue was purified by preparatory plate chromatography (50% EtOAc/Hex)

ORD-Eintrag

ord-2442c3a2a0b64919b0e37b0ce182ad8f

Quelldatensatz

uspto-grants-2001_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06214877B1