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Details for Patent: 5,554,755

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Details for Patent: 5,554,755

Title: 2-amino-3-aroyl-benzo[.beta.]thiophenes and methods for preparing and using same to produce 6-hydroxy-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 -piperidinoethoxy)benzoyl]benzo[.beta.]thiophene.
Inventor(s): Godfrey; Alexander G. (Greenwood, IN)
Assignee: Eli Lilly and Company (Indianapolis, IN)
Filing Date:Mar 15, 1995
Application Number:08/404,659
Claims:1. A method of using a compound of formula (A) ##STR8## to prepare a compound of the formula ##STR9## or the pharmaceutically acceptable salts thereof; wherein R is 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, and R.sub.1 and R.sub.2 are independently C.sub.1 -C.sub.6 alkyl, or combine to form C.sub.4 -C.sub.6 polymethylene or --(CH.sub.2).sub.2 O(CH.sub.2).sub.2 --; and

R.sub.3 and R.sub.4 are independently C.sub.1 -C.sub.6 alkyl or combine to form C.sub.4 -C.sub.6 polymethylene;

comprising acylating a compound of the formula (A) with an acylating agent of the formula ##STR10## wherein R.sub.5 is bromo, iodo, chloro, or a group forming an active ester.

2. A process according to claim 1, wherein R" is --(CH.sub.2).sub.n NR.sub.1 R.sub.2, and R.sub.5 is bromo, chloro or iodo, and the reaction is carried out in the presence of a protic acid.

3. A process according to claim 2, wherein the protic acid is hydrochloric acid.

4. A process according to claim 3, wherein the acylating agent is 4-(2-piperidinoethoxy)benzoyl chloride hydrochloride.
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