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Generated: August 22, 2017

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Title: 2-amino-3-aroyl-benzo[.beta.]thiophenes and methods for preparing and using same to produce 6-hdyroxy-2-(4-hydroxyphenyl)-3-[4-(2-aminoethoxy)-benzoyl]benzo[.beta.] thiophenes
Abstract:A group of 2-amino-3-aroyl-benzo[.beta.]thiophenes are prepared by treating an aldehyde with an anion of dimethylamino thioformamide, cyclizing the .alpha.-hydroxy thioamide, and subsequently acylating the benzo[.beta.]thiophene to yield the 2-amino-3-aryl derivative. These compounds may be treated with suitable phenyl Grignard reagents, and after deprotection, yield 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-peperidinoethoxy)benzoyl]benzo[.beta .]thiophene.
Inventor(s): Godfrey; Alexander G. (Greenwood, IN)
Assignee: Eli Lilly and Company (Indianapolis, IN)
Filing Date:Sep 10, 1996
Application Number:08/710,070
Claims:1. A process for preparing a compound of the formula ##STR8## or the pharmaceutically acceptable salts thereof; wherein

R and R' are the same or different and represent C.sub.1 -C.sub.6 alkyl; R" is C.sub.1 -C.sub.6 alkyl, amino C.sub.1 -C.sub.6 alkyl, or a group of the formula --(CH.sub.2).sub.n NR.sub.1 R.sub.2, wherein n is 1 to 4; comprising reacting a compound of the formula ##STR9## where R.sub.1 and R.sub.2 are independently C.sub.1 -C.sub.6 alkyl, or R.sub.1 and R.sub.2 combine to form C.sub.4 -C.sub.6 polymethylene or --(CH.sub.2).sub.2 O(CH.sub.2).sub.2 --; R.sub.3 and R.sub.4 are independently C.sub.1 -C.sub.4 alkyl or combine to form C.sub.4 -C.sub.6 polymethylene, with a phenyl Grignard reagent wherein the phenyl Grignard reagent is of the formula ##STR10## where X is chloro, bromo, or iodo.

2. A process according to claim 1, wherein R is methyl, R" is 2-piperidinoethyl, R.sub.3 and R.sub.4 are methyl, and the phenyl Grignard agent is a p-methoxyphenyl magnesium halide.

3. The process of claim 1 wherein the compound of the formula ##STR11## is dealkylated to form a compound of formula III ##STR12## where R.sub.6 and R.sub.7 are hydrogen.
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