Propionic Acid → N-[5-(1-Methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylmethyl]-propionamide

To a solution of 6-(5-aminomethyl-pyridin-3-yl)-1-methyl-3,4-dihydro-1H-quinolin-2-one (example 36, 0.05 g, 0.187 mmol) in dry DMF (1 mL) were added EDCI (0.039 g, 0.206 mmol), Hünig's base (0.060 g, 0.468 mmol) and propionic acid (0.021 g, 0.282 mmol) and the reaction mixture was stirred at room temperature over night. The reaction mixture was diluted with EtOAc, poured into sat. NH4Cl solution (5 mL) and extracted with EtOAc (2×10 mL). Combined organics were dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 10% MeOH(1% NH4OH)-DCM gradient to give the title compound (0.029 g, 48%) as a white solid. MS: 324.4 (M+H+).

1. extractionextracted with EtOAc (2×10 mL)
2. dry with materialCombined organics were dried over Na2SO4
3. filtrationfiltered
4. customevaporated to dryness
5. customThe residue was purified by silica gel flash chromatography
6. washeluting with a 0 to 10% MeOH(1% NH4OH)-DCM gradient

ORD 기록

ord-3ba9091975df41b0a4a8205c2da69c72

출처 데이터셋

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09260408B2