Method for synthesizing flosequinan from 4-fluoroanthranilic...

Details Method for synthesizing flosequinan from 4-fluoroanthranilic... Method for synthesizing flosequinan from 4-fluoroanthranilic...

C - Chemistry, Metallurgy

07

D

C07D 215/36 (2006.01)

Patent

CA 2386552

A high-yield, 4-step synthesis for flosequinan starting with 4- fluoroanthranilic acid comprising cyclization with phosgene to create an intermediate -A, followed by methylation to create an intermediate -B, then by reaction with dimsyl sodium to create an intermediate -C, then by reaction with triethyl orthoformate in the presence of piperdine and acetic acid to give flosequinan. The overall yield of the disclosed process is greater than about 16 %.

L'invention concerne une synthèse en 4 étapes, à rendement élevé, de floséquinan, à partir de l'acide 4-fluoroanthranilique, consistant à cycliser cet acide au moyen de phosgène afin de créer un intermédiaire -B, puis à faire réagir cet intermédiaire avec du dimsylsodium afin de créer un intermédiaire -C que l'on fait réagir avec un orthoformate de triéthyle en présence de piperdine et d'acide acétique, de manière à obtenir du floséquinan. Le rendement global obtenu à l'aide du procédé décrit est supérieur à environ 16 %.

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