Hydrogenation of 2-nitro-5-fluorobenzoic acid (I), followed by in situ condensation with acetic anhydride produced benzoxazinone (II). Subsequent reaction of (III) with 2-chloroaniline (III) in refluxing AcOH furnished quinazolinone (IV). Treatment of (IV) with 2,6-pyridinedicarboxaldehyde (V) in the presence of ZnCl2 and Ac2O gave rise to the pyridinylvinyl derivative (VI). The title amine was finally obtained by reductive amination of aldehyde (VI) with diethylamine using NaBH(OAc)3). The two atropisomers were separated by means of preparative chiral HPLC.

Hydrogenation of 2-nitro-5-fluorobenzoic acid (I), followed by in situ condensation with acetic anhydride produced benzoxazinone (II). Subsequent reaction of (III) with 2-chloroaniline (III) in refluxing AcOH furnished quinazolinone (IV). Treatment of (IV) with 2,6-pyridinedicarboxaldehyde (V) in the presence of ZnCl2 and Ac2O gave rise to the pyridinylvinyl derivative (VI). The title amine was finally obtained by reductive amination of aldehyde (VI) with diethylamine using NaBH(OAc)3). The two atropisomers were separated by means of preparative chiral HPLC.

Hydrogenation of 2-nitro-5-fluorobenzoic acid (I), followed by in situ condensation with acetic anhydride produced benzoxazinone (II). Subsequent reaction of (III) with 2-chloroaniline (III) in refluxing AcOH furnished quinazolinone (IV). Treatment of (IV) with 2,6-pyridinedicarboxaldehyde (V) in the presence of ZnCl2 and Ac2O gave rise to the pyridinylvinyl derivative (VI). The title amine was finally obtained by reductive amination of aldehyde (VI) with diethylamine using NaBH(OAc)3). The two atropisomers were separated by means of preparative chiral HPLC.