Process for preparing...

Details Process for preparing... Process for preparing...

C - Chemistry, Metallurgy

07

D

C07D 213/65 (2006.01) C07D 233/22 (2006.01) C07D 471/04 (2006.01) C07F 7/08 (2006.01) C07F 7/18 (2006.01)

Patent

CA 2647616

6,7-Dihydro-5H-imidazo[1,5-a]pyridin-8-one (I), is obtainable in high yields by: 1) a process which proceeds from a suitably protected C-(3-hydroxypyridin-2-yl)methylamine whose amine is converted to the formamide which is then cyclized to the imidazo[1,5- a]pyridine and hydrogenated to the 6,7-dihydro-5H-imidazo[1,5-a]pyridin-8-one, and suitably protected C-(3-hydroxypyridin-2-yl)methylamines can be prepared either in 2 steps proceeding from commercially available 3-hydroxy-2-cyanopyridine [932-35-4] or in 3 steps proceeding from commercially available 2-hydroxymethylpyridin-3-ol [14173-30-9]; 2) a process for preparing 4-hydroxy-1-(1H-imidazol-4-yl)butan-1-one, an intermediate from the synthesis of 6,7-dihydro-5H-imidazo[1,5-a]pyridin-8-one (formula I), as described in WO 2002/040484, proceeding from N,N-dimethyl-2-(trialkylsilanyl)imidazole-1-sulphonamide by lithiation and subsequent reaction with a suitably protected 4-hydroxybutyraldehyde, followed by oxidation of the secondary alcohol, acid-induced deprotection of the imidazole and deprotection of the alcohol functionality; 3) a process which proceeds from 5,6,7,8-tetrahydroimidazo[1,5-a]pyridine [38666-30-7], which is oxidized.

L'invention concerne une 6,7-dihydro-5H-imidazo[1,5-a]pyridin-8-one (I) pouvant être obtenue à des rendements élevés au moyen: 1) d'un procédé mis en oeuvre à partir d'une C-(3-hydroxypyridin-2-yl)methylamine protégée de manière appropriée dont une amine est convertie en formamide qui est ensuite cyclisée en une imidazo[1,5- a]pyridine et hydrogénée en une 6,7-dihydro-5H-imidazo[1,5-a]pyridin-8-one, des C-(3-hydroxypyridin-2-yl)methylamines protégées de manière appropriées pouvant être préparées en deux étapes à partir d'une 3-hydroxy-2-cyanopyridine [932-35-4] commercialement disponible ou en trois étapes à partir d'un 2-hydroxymethylpyridin-3-ol [14173-30-9] commercialement disponible; 2) d'un procédé de préparation d'une 4-hydroxy-1-(1H-imidazol-4-yl)butan-1-one, et d'un intermédiaire provenant de la synthèse d'une 6,7-dihydro-5H-imidazo[1,5-a]pyridin-8-one (formule I), telle que décrite dans WO 2002/040484, et d'un N,N-dimethyl-2-(trialkylsilanyl)imidazole-1-sulphonamide par lithiation, réaction ultérieure avec un 4-hydroxybutyraldehyde protégé de manière appropriée, suivies de l'oxydation d'un alcool secondaire, d'une déprotection induite par un acide d'imidazole et d'une déprotection de la fonctionnalité alcool; 3) un procédé mis en oeuvre à partir d'une 5,6,7,8-tetrahydroimidazo[1,5-a]pyridine [38666-30-7] qui est oxydée.

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