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32. 发明申请

US20090118512A1 Process for Preparing 6,7-Dihydro-5H-Imidazo[1,5-A]Pyridin-8-One 审中-公开
标题翻译： 6,7-二氢-5H-咪唑并[1,5-a]吡啶-8-酮的制备方法
公开(公告)号：US20090118512A1
公开(公告)日：2009-05-07
申请号：US12225813
申请日：2007-03-30
申请人： Pierre Martin , Andreas Boudier , Michael Quirmbach , Robert Mah , Nathalie Jotterand
发明人： Pierre Martin , Andreas Boudier , Michael Quirmbach , Robert Mah , Nathalie Jotterand
IPC分类号： C07D471/04 , C07D211/74 , C07F7/10 , C07D233/64
CPC分类号： C07D233/22 , C07D213/65 , C07D471/04 , C07F7/0814
摘要： 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.
摘要翻译： 6,7-二氢-5H-咪唑并[1,5-a]吡啶-8-酮（I）可以通过以下方式获得：1）从适当保护的C-（3-羟基吡啶-2 - 基）甲胺，其胺转化成甲酰胺，然后将其环化为咪唑并[1,5-a]吡啶，并氢化成6,7-二氢-5H-咪唑并[1,5-a] 一个和适当保护的C-（3-羟基吡啶-2-基）甲胺可以从市售的3-羟基-2-氰基吡啶[932-35-4]或以商业上可获得的3个步骤 2-羟甲基吡啶-3-醇[14173-30-9]; 2）制备4-羟基-1-（1H-咪唑-4-基）丁-1-酮，合成6,7-二氢-5H-咪唑并[1,5-a]吡啶的中间体 -8-（异构体I），如WO 2002/040484中所述，通过锂化从N，N-二甲基-2-（三烷基硅烷基）咪唑-1-磺酰胺进行，随后与适当保护的4-羟基丁醛反应，然后仲醇的氧化，酸诱导的咪唑脱保护和醇官能团的脱保护; 3）从被氧化的5,6,7,8-四氢咪唑并[1,5-a]吡啶[38666-30-7]进行的方法。

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