Ethyl 4-fluoro-3-chlorobenzimidate → 2-[2-(3-chloro-4-fluorophenyl)-6-hydroxy-4-oxo-4H-quinazolin-3-yl]-N-isopropylacetamide

Participants

Reaction Steps

A mixture of 2-amino-5-hydroxy-N-(isopropylcarbamoylmethyl)benzamide (INTERMEDIATE II.1) (400 mg, 1.59 mmol) and ethyl 4-fluoro-3-chlorobenzimidate*HCl (INTERMEDIATE III.5) (1.14 g, 4.78 mmol) in ethanol (10 mL) was heated at reflux temperature for 1 h. The mixture was then cooled to room temperature and the resultant solid collected by filtration and washed with additional portions of cold ethanol (3×20 mL) to afford 2-[2-(3-chloro-4-fluorophenyl)-6-hydroxy-4-oxo-4H-quinazolin-3-yl]-N-isopropylacetamide (INTERMEDIATE IV.1) (380 mg, 0.97 mmol, 61%) as a white solid.

Provenance & Evidence