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US4358593A
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Process for preparing 3-(4-aminoethoxybenzoyl)benzo[b]thiophenes
Assignee: Eli Lilly and Co
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Filing: 1981-04-03
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Granted: 1982-11-09
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Expires: 2001-04-03
Abstract
Abstract The use of particularly advantageous protecting groups for the hydroxy groups of 6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophenes provides a high-yielding process for the preparation of such compounds having a 4-(2-aminoethoxy)benzoyl 3-group.
Inventors
- 👤 Charles D. Jones
- 👤 Mary E. Goettel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 11:28
CPC Classifications
C; C07; C07D; C07D333/00; C07D333/50; C07D333/52; C07D333/54; C07D333/56; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
138 words
A process for preparing a compound of the formula ##STR8## wherein R 1 and R 2 are independently C 1 -C 4 alkyl, or combine to form C 4 -C 6 polymethylene or --(CH 2 ) 2 O(CH 2 ) 2 --; which process comprises acylating a compound of the formula ##STR9## wherein R is --COR 3 or --SO 2 CH 3 , and R 3 is methyl, phenyl, p-tolyl, p-anisyl, or mono- or di(halo or nitro)phenyl; under Friedel-Crafts conditions with an acylating agent of the formula ##STR10## wherein R 5 is X or ##STR11## X is chloro, bromo or --SO 2 R 3 ; and R 4 is chloro, bromo, iodo, or an activating ester group; when R 5 is X, displacing the X group with an amine of the formula ##STR12## and cleaving the R groups.
Claim 2
Dependent Claim
138 words
A process for preparing a compound of the formula ##STR8## wherein R 1 and R 2 are independently C 1 -C 4 alkyl, or combine to form C 4 -C 6 polymethylene or --(CH 2 ) 2 O(CH 2 ) 2 --; which process comprises acylating a compound of the formula ##STR9## wherein R is --COR 3 or --SO 2 CH 3 , and R 3 is methyl, phenyl, p-tolyl, p-anisyl, or mono- or di(halo or nitro)phenyl; under Friedel-Crafts conditions with an acylating agent of the formula ##STR10## wherein R 5 is X or ##STR11## X is chloro, bromo or --SO 2 R 3 ; and R 4 is chloro, bromo, iodo, or an activating ester group; when R 5 is X, displacing the X group with an amine of the formula ##STR12## and cleaving the R groups.
Claim 3
Dependent Claim
18 words
A process of claim 1 wherein the starting compound is a compound wherein R is --COR 3 .
Claim 4
Dependent Claim
17 words
A process of claim 2 wherein the starting compound is a compound wherein R 3 is methyl.
Claim 5
Dependent Claim
17 words
A process of claim 2 wherein the starting compound is a compound wherein R 3 is phenyl.
Claim 6
Dependent Claim
17 words
A process of claim 2 wherein the starting compound is a compound wherein R 3 is p-anisyl.
Claim 7
Dependent Claim
20 words
A process of claim 1 wherein the starting compound is a compound wherein R is --SO 2 CH 3 .
Claim 8
Dependent Claim
22 words
A process of any one of claims 1-6 wherein the acylating agent is a compound wherein R 5 is pyrrolidino or piperidino.
Claim 9
Dependent Claim
15 words
A process of claim 7 wherein the acylation is in the presence of aluminum chloride.
Claim 10
Dependent Claim
15 words
A process of claim 7 wherein the acylation is in the presence of trifluoromethanesulfonic acid.
Claim 11
Dependent Claim
19 words
A process of claim 8 wherein the acylating agent is a compound wherein R 4 is chloro or bromo.
Claim 12
Dependent Claim
19 words
A process of claim 9 wherein the acylating agent is a compound wherein R 4 is chloro or bromo.
Claim 13
Dependent Claim
20 words
A process of any one of claims 1-6 wherein the acylating agent is a compound wherein R 5 is X.
Claim 14
Dependent Claim
18 words
A process of claim 12 wherein the acylating agent is a compound wherein X is chloro or bromo.
Claim 15
Dependent Claim
15 words
A process of claim 13 wherein the acylation is in the presence of aluminum chloride.
Claim 16
Dependent Claim
19 words
A process of claim 14 wherein the acylating agent is a compound wherein R 4 is chloro or bromo.
Claim 17
Dependent Claim
15 words
A process of claim 13 wherein the acylation is in the presence of trifluoromethanesulfonic acid.
Claim 18
Dependent Claim
19 words
A process of claim 16 wherein the acylating agent is a compound wherein R 4 is chloro or bromo.
Claim 19
Dependent Claim
15 words
A process of claim 12 wherein the group X is displaced with piperidine or pyrrolidine.
Claim 20
Dependent Claim
15 words
A process of claim 13 wherein the group X is displaced with pyrrolidine or piperidine.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-11-08 | 1986-05-10 | 1986-11-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-11-08 | 1990-05-10 | 1990-11-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-11-08 | 1994-05-10 | 1994-11-09 | $7700.00 | Window Closed / Lapsed |