Diisopropylethylamine → 4-((4-Fluorobenzyl)oxy)-1-(1-methyl-2-(1,3-oxazol-5-yl)-1H-benzimidazol-6-yl)pyridin-2(1H)-one

A mixture of 1-(4-amino-3-(methylamino)phenyl)-4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one (100 mg), oxazole-5-carboxylic acid (33.3 mg), HATU (118 mg), N,N-diisopropylethylamine (0.154 ml) and DMF (2 ml) was stirred at room temperature for 2 h. The mixture was poured into saturated NaHCO3 solution and extracted with EtOAc. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The resulting residue was dissolved in AcOH (2 ml), and the mixture was stirred at 80° C. for 2 h. The mixture was concentrate in vacuo. The residue was purified by NH silica gel column chromatography (MeOH/EtOAc). The resulting solid was washed with EtOAc/hexane to give the title compound (40.7 mg) as an off-white solid.

1. extractionextracted with EtOAc
2. customThe organic layer was separated
3. washwashed with brine
4. dry with materialdried over MgSO4
5. concentrationconcentrated in vacuo
6. dissolutionThe resulting residue was dissolved in AcOH (2 ml)
7. stirringthe mixture was stirred at 80° C. for 2 h
8. concentrationThe mixture was concentrate in vacuo
9. customThe residue was purified by NH silica gel column chromatography (MeOH/EtOAc)
10. washThe resulting solid was washed with EtOAc/hexane

ORD record

ord-1c8c7164b4224003bb454c57d2d5146f

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365540B2