Process for the preparation of 4-(8-(2-chlorophenoxy)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)bicyclo[2.2.1]heptan-1-ol and novel intermediates therefor
AssigneeBristol-Meyers Squibb Company
InventorsXinhua Qian, Keming Zhu, Joerg Deerberg, Wendy Wangying Yang, Kana Yamamoto, Matthew R. Hickey
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Abstract
A process is provided for preparing 4-(8-(2-chlorophenoxy)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)bicyclo[2.2.1]heptan-1-ol and novel intermediates used in the process. The compound is a 11-beta hydroxysteroid dehydrogenase type I inhibitor which exhibits activity in the treatment of various metabolic diseases.
Claims11
A compound of the structure
A process for preparing intermediate 1 of the structure
- which comprises treating a dialcohol compound of the structure
- with an aqueous mineral acid selected from HCl and H2SO4.
A process for preparing Compound 2 of the structure
- which comprises subjecting Compound 1 of the structure
- to oxidation to form the acid intermediate 2.
A process for preparing compound 3 of the structure
- which comprises reacting the acid
- with a hydrazide salt of the structure
- and 2-chloro-4,5-dihydro-1,3-dimethyl-1H-imidazoline chloride
- at a reduced temperature to form compound 3.
A process for preparing compound I of the structure
- which comprises treating Compound 3 of the structure
- with a carboxylic acid to form compound I.
A process for preparing compound I of the structure
- which comprises subjecting Compound 1 of the structure
- to oxidation to form compound 2
- reacting compound 2 with a hydrazide salt of the structure
- and 2-chloro-4,5-dihydro-1,3-dimethyl-1H-imidazoline chloride
- at a reduced temperature to form the pyridine hydrazide intermediate 3 of the structure
- and treating compound 3 with a carboxylic acid to form Compound I.
Dependencies are inferred from the claim text.