Deprotection method for tetrazole compound
US-2015239854-A1 · Aug 27, 2015 · US
Method for producing biaryl compound
US9624181B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-9624181-B2 |
| Application number | US-201314424912-A |
| Country | US |
| Kind code | B2 |
| Filing date | Aug 30, 2013 |
| Priority date | Aug 31, 2012 |
| Publication date | Apr 18, 2017 |
| Grant date | Apr 18, 2017 |
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Abstract
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The invention provides a production method of a biaryl compound of the formula [3] or a salt thereof, including reacting a 2-phenylazole derivative of the formula [1] or a salt thereof, with a benzene derivative of the formula [2] or a salt thereof in the presence of a metal catalyst, a base, and one or more of (a) a monocarboxylic acid metal salt, (b) a dicarboxylic acid metal salt, (c) a sulfonic acid metal salt, and (d) a phosphate or phosphoric amide metal salt represented by R A x P(O)(OM) y wherein each symbol is as defined herein.
First claim
Opening claim text (preview).
The invention claimed is: 1. A method of producing a biaryltetrazole compound represented by the formula [3′]: wherein R 1 to R 4 are each independently a hydrogen atom, or an alkyl group, an aralkyl group or an aryl group, each of which optionally has 1 to 5 substituents that are the same or different and that are selected from (1) halogen atom; (2) hydroxy; (3) amino; (4) nitro; (5) cyano; (6) a heterocyclic group optionally substituted by 1 to 3 substituents selected from halogen atom, hydroxy, amino, nitro, cyano, optionally halogenated C 1-6 alkyl, mono- or di-C 1-6 alkyl-amino, C 6-14 aryl, mono- or di-C 6-14 aryl-amino, C 3-8 cycloalkyl, C 1-6 alkoxy, C 1-6 alkoxy-C 1-6 alkoxy, C 1-6 alkylsulfanyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, optionally esterified carboxy, carbamoyl, thiocarbamoyl, mono- or di-C 1-6 alkyl-carbamoyl, mono- or di-C 6-14 aryl-carbamoyl, sulfamoyl, mono- or di-C 1-6 alkyl-sulfamoyl, and mono- or di-C 6-14 aryl-sulfamoyl; (7) mono- or di-C 1-6 alkyl-amino; (8) mono- or di-C 6-14 aryl-amino; (9) mono- or di-C 7-14 aralkyl-amino; (10) N-C 1-6 alkyl-N-C 6-14 aryl-amino; (11) N-C 1-6 alkyl-N-C 7-14 aralkyl-amino; (12) C 3-8 cycloalkyl; (13) optionally halogenated C 1-6 alkoxy; (14) C 1-6 alkylsulfanyl; (15) C 1-6 alkylsulfinyl; (16) C 1-6 alkylsulfonyl; (17) optionally esterified carboxy; (18) C 1-6 alkyl-carbonyl; (19) C 3-8 cycloalkyl-carbonyl; (20) C 6-14 aryl-carbonyl; (21) carbamoyl; (22) thiocarbamoyl; (23) mono- or di-C 1-6 alkyl-carbamoyl; (24) mono- or di-C 6-14 aryl-carbamoyl; (25) N-C 1-6 alkyl-N-C 6-14 aryl-carbamoyl; (26) mono- or di-5- to 7-membered heterocyclyl-carbamoyl; (27) C 1-6 alkyl-carbonylamino optionally substituted by carboxy; (28) C 6-14 aryloxy optionally substituted by 1 to 3 substituents selected from halogen atom, hydroxy, amino, nitro, cyano, optionally halogenated C 1-6 alkyl, mono- or di-C 1-6 alkyl-amino, C 6-14 aryl, mono- or di-C 6-14 aryl-amino, C 3-8 cycloalkyl, C 1-6 alkoxy, C 1-6 alkoxy-C 1-6 alkoxy, C 1-6 alkylsulfanyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, optionally esterified carboxy, carbamoyl, thiocarbamoyl, mono- or di-C 1-6 alkyl-carbamoyl, mono- or di-C 6-14 aryl-carbamoyl, sulfamoyl, mono- or di-C 1-6 alkyl-sulfamoyl and mono- or di-C 6-14 aryl-sulfamoyl; (29) C 6-14 aryl optionally substituted by 1 to 3 substituents selected from halogen atom, hydroxy, amino, nitro, cyano, optionally halogenated C 1-6 alkyl, mono- or di-C 1-6 alkyl-amino, C 6-14 aryl, mono- or di-C 6-14 aryl-amino, C 3-8 cycloalkyl, C 1-6 alkoxy, C 1-6 alkoxy-C 1-6 alkoxy, C 1-6 alkylsulfanyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, optionally esterified carboxy, carbamoyl, thiocarbamoyl, mono- or di-C 1-6 alkyl-carbamoyl, mono- or di-C 6-14 aryl-carbamoyl, sulfamoyl, mono- or di-C 1-6 alkyl-sulfamoyl and mono- or di-C 6-14 aryl-sulfamoyl; (30) heterocyclyl-oxy; (31) sulfamoyl; (32) mono- or di-C 1-6 alkyl-sulfamoyl; (33) mono- or di-C 6-14 aryl-sulfamoyl; (34) C 7-14 aralkyloxy optionally substituted by 1 to 3 substituents selected from halogen atom, hydroxy, amino, nitro, cyano, optionally halogenated C 1-6 alkyl, mono- or di-C 1-6 alkyl-amino, C 6-14 aryl, mono- or di-C 6-14 aryl-amino, C 3-8 cycloalkyl, C 1-6 alkoxy, C 1-6 alkoxy-C 1-6 alkoxy, C 1-6 alkylsulfanyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, optionally esterified carboxy, carbamoyl, thiocarbamoyl, mono- or di-C 1-6 alkyl-carbamoyl, mono- or di-C 6-14 aryl-carbamoyl, sulfamoyl, mono- or di-C 1-6 alkyl-sulfamoyl and mono- or di-C 6-14 aryl-sulfamoyl; (35) C 1-6 alkyl-carbonyloxy; (36) C 1-6 alkoxy-carbonyl; and (37) tri-C 1-6 alkylsilyloxy; R 5′ is a methyl group, a methyl group substituted by a protected hydroxyl group, or a lower alkoxycarbonyl group, and R 6 is a tetrazolyl-protecting group, or a salt thereof, comprising reacting a 2-phenylazole derivative represented by the formula [1′]: wherein R 1 to R 4 are each independently a hydrogen atom, or an alkyl group, an aralkyl group or an aryl group, each of which optionally has 1 to 5 substituents that are the same or different and that are selected from (1) halogen atom; (2) hydroxy; (3) amino; (4) nitro; (5) cyano; (6) a heterocyclic group optionally substituted by 1 to 3 substituents selected from halogen atom, hydroxy, amino, nitro, cyano, optionally halogenated C 1-6 alkyl, mono- or di-C 1-6 alkyl-amino, C 6-14 aryl, mono- or di-C 6-14 aryl-amino, C 3-8 cycloalkyl, C 1-6 alkoxy, C 1-6 alkoxy-C 1-6 alkoxy, C 1-6 alkylsulfanyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, optionally esterified carboxy, carbamoyl, thiocarbamoyl, mono- or di-C 1-6 alkyl-carbamoyl, mono- or di-C 6-14 aryl-carbamoyl, sulfamoyl, mono- or di-C 1-6 alkyl-sulfamoyl, and mono- or di-C 6-14 aryl-sulfamoyl; (7) mono- or di-C 1-6 alkyl-amino; (8) mono- or di-C 6-14 aryl-amino; (9) mono- or di-C 7-14 aralkyl-amino; (10) N-C 1-6 alkyl-N-C 6-14 aryl-amino; (11) N-C 1-6 alkyl-N-C 7-14 aralkyl-amino; (12) C 3-8 cycloalkyl; (13) optionally halogenated C 1-6 alkoxy; (14) C 1-6 alkylsulfanyl; (15) C 1-6 alkylsulfinyl; (16) C 1-6 alkylsulfonyl; (17) optionally esterified carboxy; (18) C 1-6 alkyl-carbonyl; (19) C 3-8 cycloalkyl-carbonyl; (20) C 6-14 aryl-carbonyl; (21) carbamoyl; (22) thiocarbamoyl; (23) mono- or di-C 1-6 alkyl-carbamoyl; (24) mono- or di-C 6-14 aryl-carbamoyl; (25) N-C 1-6 alkyl-N-C 6-14 aryl-carbamoyl; (26) mono- or di-5- to 7-membered heterocyclyl-carbamoyl; (27) C 1-6 alkyl-carbonylamino optionally substituted by carboxy; (28) C 6-14 aryloxy optionally substituted by 1 to 3 substituents selected from halogen atom, hydroxy, amino, nitro, cyano, optionally halogenated C 1-6 alkyl, mono- or di-C 1-6 alkyl-amino, C 6-14 aryl, mono- or di-C 6-14 aryl-amino, C 3-8 cycloalkyl, C 1-6 alkoxy, C 1-6 alkoxy-C 1-6 alkoxy, C 1-6 alkylsulfanyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, optionally esterified carboxy, carbamoyl, thiocarbamoyl, mono- or di-C 1-6 alkyl-carbamoyl, mono- or di-C 6-14 aryl-carbamoyl, sulfamoyl, mono- or di-C 1-6 alkyl-sulfamoyl and mono- or di-C 6-14 aryl-sulfamoyl; (29) C 6-14 aryl optionally substituted by 1 to 3 substituents selected from halogen atom, hydroxy, amino, nitro, cyano, optionally halogenated C 1-6 alkyl, mono- or di-C 1-6 alkyl-amino, C 6-14 aryl, mono- or di-C 6-14 aryl-amino, C 3-8 cycloalkyl, C 1-6 alkoxy, C 1-6 alkoxy-C 1-6 alkoxy, C 1-6 alkylsulfanyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, optionally esterified carboxy, carbamoyl, thiocarbamoyl, mono- or di-C 1-6 alkyl-carbamoyl, mono- or di-C 6-14 aryl-carbamoyl, sulfamoyl, mono- or di-C 1-6 alkyl-sulfamoyl and mono- or di-C 6-14 aryl-sulfamoyl; (30) heterocyclyl-oxy; (31) sulfamoyl; (32) mono- or di-C 1-6 alkyl-sulfamoyl; (33) mono- or di-C 6-14 aryl-sulfamoyl; (34) C 7-14 aralkyloxy optionally substituted by 1 to 3 substituents selected from halogen atom, hydroxy, amino, nitro, cyano, optionally halogenated C 1-6 alkyl, mono- or di-C 1-6 alkyl-amino, C 6-14 aryl, mono- or di-C 6-14 aryl-amino, C 3-8 cycloalkyl, C 1-6 alkoxy, C 1-6 alkoxy-C 1-6 alkoxy, C 1-6 alkylsulfanyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, optionally esterified carboxy, carbamoyl, thiocarbamoyl, mono- or di-C 1-6 alkyl-carbamoyl, mono- or di-C 6-14 aryl-carbamoyl, sulfamoyl, mono- or di-C 1-6 alkyl-sulfamoyl and mono- or di-C 6-14 aryl-sulfamoyl; (35) C 1-6 alkyl-carbonyloxy; (36) C 1-6 alkoxy-carbonyl; and (37) tri-C 1-6 alkylsilyloxy; and R 6 is a tetrazo
Assignees
Inventors
Classifications
- C07D257/04Primary
Five-membered rings · CPC title
Substitution · CPC title
linked by a carbon chain containing aromatic rings · CPC title
containing three or more hetero rings · CPC title
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- What does patent US9624181B2 cover?
- The invention provides a production method of a biaryl compound of the formula [3] or a salt thereof, including reacting a 2-phenylazole derivative of the formula [1] or a salt thereof, with a benzene derivative of the formula [2] or a salt thereof in the presence of a metal catalyst, a base, and one or more of (a) a monocarboxylic acid metal salt, (b) a dicarboxylic acid metal salt, (c) a sulf…
- Who is the assignee on this patent?
- Api Corp
- What technology area does this patent fall under?
- Primary CPC classification C07D257/04. Mapped technology areas include Chemistry & Metallurgy.
- When was this patent published?
- Publication date Tue Apr 18 2017 00:00:00 GMT+0000 (Coordinated Universal Time) (B2). Legal status and post-grant events are not shown on this page.
- What related patents are in patentsdb?
- We list 1 related publication on this page (citations in our corpus or others sharing the same primary CPC).