Diisopropylethylamine → 1-(6-(4-((4-Fluorobenzyl)oxy)-2-oxopyridin-1(2H)-yl)-1-methyl-1H-benzimidazol-2-yl)cyclopropanecarbonitrile

To a solution of 1-(4-amino-3-(methylamino)phenyl)-4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one (73 mg), 1-cyanocyclopropanecarboxylic acid (25.1 mg) and N,N-diisopropylethylamine (0.11 ml) in DMF (2 ml) was added HATU (86 mg), and the mixture was stirred at room temperature overnight. The mixture was poured into a mixture of EtOAc and water, and the organic layer was washed with brine, dried over MgSO4, and concentrated. Then the resulting residue was heated in AcOH (1 ml) at 90° C. for 1 h. The mixture was concentrated, and poured into saturated NaHCO3. The mixture was extracted with EtOAc, and the organic layer was washed with brine, dried over MgSO4, concentrated, and purified by NH silica gel column chromatography (hexane/EtOAc) to give the title compound (8 mg) as a white solid.

1. washthe organic layer was washed with brine
2. dry with materialdried over MgSO4
3. concentrationconcentrated
4. temperatureThen the resulting residue was heated in AcOH (1 ml) at 90° C. for 1 h
5. concentrationThe mixture was concentrated
6. additionpoured into saturated NaHCO3
7. extractionThe mixture was extracted with EtOAc
8. washthe organic layer was washed with brine
9. dry with materialdried over MgSO4
10. concentrationconcentrated
11. custompurified by NH silica gel column chromatography (hexane/EtOAc)

ORDレコード

ord-2d6e5c4b264d46b5b168b790d3d570b3

出典データセット

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09365540B2