1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-Methoxy-isoxazole-5-carboxylic acid [5-(1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylmethyl]-amide

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 DCM (1 mL) were added EDCI (0.039 g, 0.206 mmol), hydroxybenzotriazole (0.032 g, 0.206 mmol), Hünig's base (0.060 g, 0.468 mmol) and 3-methoxy-isoxazole-5-carboxylic acid (0.040 g, 0.281 mmol) and the resulting solution was stirred at room temperature over night. The reaction mixture was diluted with EtOAc, poured into sat. NaHCO3 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 (0.03 g, 41%) as a white solid. MS: 393.1 (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 record

ord-6a707f30f0dc4966a92b6a1019d537f9

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09260408B2