Propionic Acid → 4-((4-Chlorobenzyl)oxy)-1-(2-ethyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

HATU (321 mg) was added to a solution of 1-(4-amino-3-(methylamino)phenyl)-4-((4-chlorobenzyl)oxy)pyridin-2(1H)-one (250 mg), N,N-diisopropylethylamine (0.367 ml) and propionic acid (57.3 mg) in DMF (3 ml) at room temperature. The mixture was stirred at room temperature for 1 h. The mixture was quenched with brine and extracted with EtOAc. The organic layer was separated, washed with brine, dried over MgSO4, and concentrated in vacuo. The resulting residue in AcOH (1 ml) was stirred at 80° C. for 1 h. After evaporation of the solvent, the residue was purified by NH silica gel column chromatography (hexane/EtOAc to MeOH/EtOAc). The resulting solid was recrystallized twice from EtOH followed by THF to give the title compound (114 mg) as a white solid.

1. customThe mixture was quenched with brine
2. extractionextracted with EtOAc
3. customThe organic layer was separated
4. washwashed with brine
5. dry with materialdried over MgSO4
6. concentrationconcentrated in vacuo
7. stirringThe resulting residue in AcOH (1 ml) was stirred at 80° C. for 1 h
8. customAfter evaporation of the solvent
9. customthe residue was purified by NH silica gel column chromatography (hexane/EtOAc to MeOH/EtOAc)
10. customThe resulting solid was recrystallized twice from EtOH

ORD-Eintrag

ord-10fd3783cb66416a8083a809fdc70b88

Quelldatensatz

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09365540B2