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). Rf =0.30 (hexane:ethyl acetate=2:1) IR (CHCl3): 3450, 3000, 1640, 1515, 1490, 1420, 1230, 1070, 780 cm-1.

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 record

ord-c4a530655f404be9a7816cdcb58fa387

Source dataset

uspto-grants-1994_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05369109