US5874581A
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2-silyloxy-tetrahydrothienopyridine, salt thereof and process for preparing the same
Assignee: Ube Corp
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Filing: 1995-10-04
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Granted: 1999-02-23
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Expires: 2015-10-04
Abstract
Abstract PCT No. PCT/JP95/02023 Sec. 371 Date Mar. 31, 1997 Sec. 102(e) Date Mar. 31, 1997 PCT Filed Oct. 4, 1995 PCT Pub. No. WO96/11203 PCT Pub. Date Apr. 18, 1996A 2-silyloxy-4,5,6,7-tetrahydrothieno[3,2-c]pyridine represented by the formula (I): <IMAGE> (I) wherein R1, R2 and R3 each independently represent an alkyl group having 1 to 10 carbon atoms or an aryl group, and a salt thereof and a process for preparing the same, and a 5-alkyl-2-silyloxy-4,5,6,7-tetrahydrothieno[3,2-c]-pyridine represented by the formula (IV): <IMAGE> (IV) wherein R1, R2 and R3 represent the same meanings as described above; R4 represents a hydrogen atom, an alkoxycarbonyl group having 2 to 10 carbon atoms, an acyl group having 2 to 10 carbon atoms or a cyclo-alkylcarbonyl group having 4 to 10 carbon atoms; and R5 represents a halogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, which is useful as a synthetic intermediate of an antiplatelet medicine and an elastase inhibitor, etc., and a process for preparing the same.
Inventors
- 👤 Kikuo Ataka
- 👤 Hiroyuki Miyata
- 👤 Masahiko Kohno
- 👤 Naoyuki Yokota
- 👤 Yasuhito Yamamoto
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 18:11
CPC Classifications
C; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
38 words
A 2-silyloxy-4,5,6,7-tetrahydrothieno 3,2-c!pyridine represented by the formula (I): ##STR23## wherein R 1 , R 2 and R 3 each independently represent an alkyl group having 1 to 10 carbon atoms or an aryl group, or a salt thereof.
Claim 2
Dependent Claim
38 words
A 2-silyloxy-4,5,6,7-tetrahydrothieno 3,2-c!pyridine represented by the formula (I): ##STR23## wherein R 1 , R 2 and R 3 each independently represent an alkyl group having 1 to 10 carbon atoms or an aryl group, or a salt thereof.
Claim 3
Dependent Claim
29 words
The 2-silyloxy-4,5,6,7-tetrahydrothieno 3,2-c!pyridine or a salt thereof according to claim 1, wherein R 1 to R 3 are alkyl groups having 1 to 5 carbon atoms or phenyl groups.
Claim 4
Dependent Claim
40 words
The 2-silyloxy-4,5,6,7-tetrahydrothieno 3,2-c!pyridine and a salt thereof according to claim 1, wherein said compound is selected from the group consisting of: 2-(tert-butyldimethylsilyloxy)-4,5,6,7-tetrahydrothieno 3,2-c!pyridine and a salt thereof, 2-triisopropylsilyloxy-4,5,6,7-tetrahydrothieno 3,2-c!pyridine and a salt thereof, and 2-(tert-butyldiphenylsilyloxy)-4,5,6,7-tetrahydrothieno 3,2-c!pyridine and a salt thereof.
Claim 5
Dependent Claim
97 words
A process for preparing a 2-silyloxy-4,5,6,7-tetrahydrothieno 3,2-c!pyridine represented by the formula (I): ##STR24## wherein R 1 , R 2 and R 3 each independently represent an alkyl group having 1 to 10 carbon atoms or an aryl group; which comprises allowing a 5,6,7,7a-tetrahydro-4H-thieno- 3,2-c!pyridin-2-one represented by the formula (II): ##STR25## or a tautomer thereof to react with a halogenated silane represented by the formula (III): ##STR26## wherein R 1 , R 2 and R 3 represent the same meanings as described in claim 1, and X represents a halogen atom, in the presence of a tertiary amine.
Claim 6
Dependent Claim
15 words
The preparation process according to claim 4, wherein the tertiary amine is triethylamine or diisopropylethylamine.
Claim 7
Dependent Claim
24 words
The preparation process according to claim 4, wherein the halogenated silane is a compound selected from the group consisting of tert-butyldimethylchlorosilane, tert-butyldiphenylchlorosilane and triisopropylchlorosilane.
Claim 8
Dependent Claim
94 words
A 5-alkyl-2-silyloxy-4,5,6,7-tetrahydrothieno 3,2-c!-pyridine represented by the formula (IV): ##STR27## wherein R 1 , R 2 and R 3 each independently represent an alkyl group having 1 to 10 carbon atoms or an aryl group; R 4 represents a hydrogen atom, an alkoxycarbonyl group having 2 to 10 carbon atoms, an acyl group having 2 to 10 carbon atoms or a cycloalkylcarbonyl group having 4 to 10 carbon atoms; and R 5 represents a halogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.
Claim 9
Dependent Claim
94 words
A 5-alkyl-2-silyloxy-4,5,6,7-tetrahydrothieno 3,2-c!-pyridine represented by the formula (IV): ##STR27## wherein R 1 , R 2 and R 3 each independently represent an alkyl group having 1 to 10 carbon atoms or an aryl group; R 4 represents a hydrogen atom, an alkoxycarbonyl group having 2 to 10 carbon atoms, an acyl group having 2 to 10 carbon atoms or a cycloalkylcarbonyl group having 4 to 10 carbon atoms; and R 5 represents a halogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.
Claim 10
Dependent Claim
25 words
The 5-alkyl-2-silyloxy-4,5,6,7-tetrahydrothieno 3,2-c!pyridine according to claim 7, wherein R 1 to R 3 are alkyl groups having 1 to 5 carbon atoms or phenyl groups.
Claim 11
Dependent Claim
63 words
The 5-alkyl-2-silyloxy-4,5,6,7-tetrahydrothieno 3,2-c!pyridine according to claim 7, wherein R 4 is selected from the group consisting of a hydrogen atom, an alkoxycarbonyl group wherein the alkyl group portion has 1 to 5 carbon atoms, an acyl group wherein the alkyl group portion has 1 to 5 carbon atoms and a cycloalkylcarbonyl group wherein the cycloalkyl group portion has 3 to 6 carbon atoms.
Claim 12
Dependent Claim
42 words
The 5-alkyl-2-silyloxy-4,5,6,7-tetrahydrothieno 3,2-c!pyridine according to claim 7, wherein R 5 is selected from the group consisting of a fluorine atom, a chlorine atom, an alkyl group having 1 to 3 carbon atoms and an alkoxy group having 1 to 3 carbon atoms.
Claim 13
Dependent Claim
35 words
The 5-alkyl-2-silyloxy-4,5,6,7-tetrahydrothieno 3,2-c!pyridine according to claim 7, wherein said compound is selected from the group consisting of: 2-(tert-butyldimethylsilyloxy)-5-(2-chlorobenzyl)-4,5,6,7-tetrahydrothieno3,2-c!pyridine, 2-(tert-butyldimethylsilyloxy)-5-(2-fluorobenzyl)-4,5,6,7-tetrahydrothieno3,2-c!pyridine, 2-(tert-butyldimethylsilyloxy)-5-(α-methoxycarbonyl-2-chlorobenzyl)-4,5,6,7-tetrahydrothieno 3,2-c!pyridine, 2-(tert-butyldiphenylsilyloxy)-5-(2-chlorobenzyl)-4,5,6,7-tetrahydrothieno3,2-c!pyridine, 2-triisopropylsilyloxy-5-(2-chlorobenzyl)-4,5,6,7-tetrahydrothieno 3,2-c!pyridine, 2-(tert-butyldimethylsilyloxy)-5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno 3,2-c!pyridine, 2-triisopropylsilyloxy-5-(α-cyclopropylcarbonyl-2-chlorobenzyl)-4,5,6,7-tetrahydrothieno 3,2-c!pyridine, 2-(tert-butyldimethylsilyloxy)-5-(α-cyclopropylcarbonyl-2-chlorobenzyl)-4,5,6,7-tetrahydrothieno 3,2-c!pyridine, 2-(tert-butyldiphenylsilyloxy)-5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno 3,2-c!pyridine, and 2-(tert-butyldiphenylsilyloxy)-5-αcydclopropylcarbonyl-2-carbonyl-2-chlorobenzyl)-4,5,6,7-tetrahydrothieno 3,2-c!pyridine.
Claim 14
Dependent Claim
171 words
A process for preparing a 5-alkyl-2-silyloxy-4,5,6,7-tetrahydrothieno 3,2-c!pyridine represented by the formula (IV): ##STR28## wherein R 1 , R 2 and R 3 each independently represent an alkyl group having 1 to 10 carbon atoms or an aryl group; R 4 represents a hydrogen atom, an alkoxycarbonyl group having 2 to 10 carbon atoms, an acyl group having 2 to 10 carbon atoms or a cycloalkylcarbonyl group having 4 to 10 carbon atoms; R 5 represents a halogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms; which comprises allowing a 2-silyloxy-4,5,6,7-tetrahydrothieno 3,2-c!pyridine represented by the formula (I): ##STR29## wherein R 1 , R 2 and R 3 represent the same meanings as described in claim 1, or a salt thereof to react with a halogenated alkyl represented by the formula (VII): ##STR30## wherein R 4 and R 5 represent the same meanings as described in claim 7, and X represents a halogen atom, in the presence of a tertiary amine.
Claim 15
Dependent Claim
41 words
The preparation process according to claim 12, wherein the 2-silyloxy-4,5,6,7-tetrahydrothieno 3,2-c!pyridine compound is selected from the group consisting of: 2-(tert-butyldimethylsilyloxy)-4,5,6,7-tetrahydrothieno 3,2-c!pyridine and a salt thereof, 2-triisopropylsilyloxy-4,5,6,7-tetrahydrothieno 3,2-c!pyridine and a salt thereof, and 2- (tert-butyldiphenylsilyloxy) -4,5,6, 7-tetrahydrothieno 3,2-c!pyridine and a salt thereof.
Claim 16
Dependent Claim
29 words
The preparation process according to claim 12, wherein the halogenated alkyl is a compound selected from the group consisting of 2-chlorobenzyl chloride, 2-fluorobenzyl chloride, 2-chloro-α-methoxycarbonylbenzyl bromide and 2-fluoro-α-cyclopropylcarbonylbenzyl chloride.
Claim 17
Dependent Claim
16 words
The preparation process according to claim 12, wherein the tertiary amine is triethylamine, tributylamine or diisopropylethylamine.
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