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

Temperature

90 °C

A mixture of 1-(4-amino-3-(methylamino)phenyl)-4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one (90 mg), HATU (106 mg), propionic acid (0.040 ml), N,N-diisopropylethylamine (0.136 ml) and DMF (2 ml) was stirred at room temperature under a dry atmosphere (CaCl2 tube) for 1 h. The mixture was quenched with water and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The resulting residue was dissolved in AcOH (2 ml), and the mixture was stirred at 90° C. for 1 h. After evaporation of the solvent, the residue was purified by NH silica gel column chromatography (hexane/EtOAc). The resulting solid was recrystallized from EtOAc/MeOH to give the title compound (44.9 mg) as an off-white solid.

1. customThe mixture was quenched with water
2. extractionextracted with EtOAc
3. customThe organic layer was separated
4. washwashed with water and brine
5. dry with materialdried over MgSO4
6. concentrationconcentrated in vacuo
7. dissolutionThe resulting residue was dissolved in AcOH (2 ml)
8. customAfter evaporation of the solvent
9. customthe residue was purified by NH silica gel column chromatography (hexane/EtOAc)
10. customThe resulting solid was recrystallized from EtOAc/MeOH

ORD record

ord-5352d093cd54494593ea81ec5a336de4

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365540B2