Diisopropylamine → N-methoxy-N-methyl-3-{2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl}-3-hydroxypropanamide

Butyllithium (1.64M hexane solution, 7.54 ml, 12.4 mmol) was added to a THF (40 ml) solution of diisopropylamine (1.25 g, 12.4 mmol) at -78 ° C., and the mixture was stirred for 15 minutes. Thereto was added a THF (20 ml) solution of N-methoxy-N-methylacetamide (1.27 g, 12.3 mmol) at -78 ° C., and the resulting mixture was stirred at -78 ° C. for 15 minutes. To this mixture was added a THF (40 ml) solution of 2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline (3.00 g, 10.3 mmol). The reaction mixture was stirred at -78 ° C. to room temperature over a period of 3 hours before quenching with water and extraction with diethyl ether. The ethereal organic layer was washed with saturated sodium chloride aq solution, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by column chromatography (hexane:ethyl acetate=2:1) to give N-methoxy-N-methyl-3 -{2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-yl}-3-hydroxypropanamide (3.70 g, 91% yield).

1. stirringthe resulting mixture was stirred at -78 ° C. for 15 minutes
2. stirringThe reaction mixture was stirred at -78 ° C. to room temperature over a period of 3 hours
3. custombefore quenching with water and extraction with diethyl ether
4. washThe ethereal organic layer was washed with saturated sodium chloride aq solution
5. dry with materialdried over magnesium sulfate
6. concentrationconcentrated in vacuo
7. customThe residue was purified by column chromatography (hexane:ethyl acetate=2:1)

ORD-Eintrag

ord-6b7077081fe44bf986ba39e7250ec26b

Quelldatensatz

uspto-grants-1994_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05276154