Diisopropylethylamine → 4-((4-Fluorobenzyl)oxy)-1-(1-methyl-2-(2-methylcyclopropyl)-1H-benzimidazol-6-yl)pyridin-2(1H)-one

HATU (235 mg) was added to a solution of 1-(4-amino-3-(methylamino)phenyl)-4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one (200 mg), N,N-diisopropylethylamine (0.308 ml) and 2-methylcyclopropanecarboxylic acid (0.057 ml) 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 twice. 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 passed through NH silica pad and concentrated in vacuo. The resulting solid was recrystallized from THF to give the title compound as a white solid.

1. customThe mixture was quenched with brine
2. extractionextracted with EtOAc twice
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. concentrationconcentrated in vacuo
10. customThe resulting solid was recrystallized from THF

ORD record

ord-f6717387180a450197cad4ddccee1049

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365540B2