5-amino-7-fluoroquinolin-2(1H)-one → HCID 91409687, compound

Participants

Reaction Steps

In the same way as in Example 137, 45 mg (0.13 mmol) of (2R,4R/S)-4-(3-ethyl-4-fluoro-2-methoxyphenyl)-2-hydroxy-2-(trifluoromethyl)hexanal, 23 mg (0.13 mmol) of 5-amino-7-fluoroquinolin-2(1H)-one and 0.09 ml (0.27 mmol) of titanium tert-butoxide are reacted to give 5-{[(2R,4R/S)-4-(3-ethyl-4-fluoro-2-methoxyphenyl)-2-hydroxy-2-(trifluoromethyl)hexylidene]amino}-7-fluoroquinolin-2(1H)-one. 80 mg of crude imine are cyclized in the same way as in Example 137 at −30° C. with 1.3 ml (1.3 mmol) of 1 M boron tribromide solution. Purification by column chromatography on silica gel (hexane/isopropanol 16%) and subsequent preparative thin-layer chromatography on an amine phase (Merck NH2F254, ethyl acetate/triethylamine, 2%) yield 7 mg of the title compound and 5 mg of the corresponding (8R)-diastereomer.

Provenance & Evidence