Patent ID: 6780993
Filing Date: 2004-08-24
Classification: C07D

Abstract:
A process for preparing 1-C-(9-deazaaden-9-yl)-1,4-imino-D-5â€²-deoxy-5â€²-methylthioribitol) and salts which comprises:a) converting a 4-cyanomethyl-6-substututed-methyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester to the corresponding methyl sulfanyl compound, 4-cyanomethyl-2,2-dimethyl-6-methylsulfanylmethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester by reaction with toluenesulfonylchloride in the presence of a base; b) methylating the product from a) to form the corresponding methylsulfanyl derivative; c) reacting the methylsulfanyl derivative from b) with tert-butoxy-bis(N,N-dimethylamino)methane to provide the corresponding 4-(1-cyano-2 dimethylamino-vinyl)-2,2-dimethyl-6-methylsulfanylmethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester; d) converting the product from c) to the corresponding 4-(1-cyano-2-hydroxy-vinyl)-2,2-dimethyl-6-methylsulfanylmethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester by reacting with a hydrolyzing agent; e) converting the product from d) to the corresponding cyanomethylamino compound by reacting with amino acetonitrile; f) converting the product from e)to the ester form by reacting with an esterification agent; g) cyclizing the product from f) to the corresponding pyrrol compound, 4-(4-amino-5-cyano-1-ethoxycarbonyl-1H-pyrrol-3-yl)-2,2-dimethyl-6-methylsulfanylmethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester; h) converting the product from g) to the corresponding amino derivative by removal of the ethoxycarbonyl sub stituent to produce 4-(4-amino-5-cyano-1H-pyrrol-3-yl)-2,2-dimethyl-6-methylsulfanylmethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester; i) reacting the product from h) with formamidine acetate to form the target compound, 1-C-(9-deazaaden-9-yl)-1,4-imino-D-5â€²-deoxy-5â€²-methylthioribitol).