AR065859A1 - ESTER OF 2,5-DIOXO-PIRROLIDIN-1-ILO OF ACID 4-BROMO-3-METIL-5-PROPOXITIOFEN-2- CARBOXILICO, ITS REGIO-SPECIFIC SYNTHESIS AND AN INTERMEDIATE OF THE SAME - Google Patents
ESTER OF 2,5-DIOXO-PIRROLIDIN-1-ILO OF ACID 4-BROMO-3-METIL-5-PROPOXITIOFEN-2- CARBOXILICO, ITS REGIO-SPECIFIC SYNTHESIS AND AN INTERMEDIATE OF THE SAMEInfo
- Publication number
- AR065859A1 AR065859A1 ARP080101261A ARP080101261A AR065859A1 AR 065859 A1 AR065859 A1 AR 065859A1 AR P080101261 A ARP080101261 A AR P080101261A AR P080101261 A ARP080101261 A AR P080101261A AR 065859 A1 AR065859 A1 AR 065859A1
- Authority
- AR
- Argentina
- Prior art keywords
- methyl
- ester
- propoxythiophene
- carboxylic acid
- dioxo
- Prior art date
Links
- 239000002253 acid Substances 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- XAOJMTRGEZJSQN-UHFFFAOYSA-N 3-methyl-5-propoxythiophene-2-carboxylic acid Chemical compound CCCOC1=CC(C)=C(C(O)=O)S1 XAOJMTRGEZJSQN-UHFFFAOYSA-N 0.000 abstract 4
- VWFVJVPPXXCWAW-UHFFFAOYSA-N 4-bromo-3-methyl-5-propoxythiophene-2-carboxylic acid Chemical compound CCCOC=1SC(C(O)=O)=C(C)C=1Br VWFVJVPPXXCWAW-UHFFFAOYSA-N 0.000 abstract 3
- -1 alkali metal propoxide salt Chemical class 0.000 abstract 3
- 239000003795 chemical substances by application Substances 0.000 abstract 3
- 239000002798 polar solvent Substances 0.000 abstract 3
- MWHJEWBLTYDUKD-UHFFFAOYSA-N 2-iodo-4-methylthiophene Chemical compound CC1=CSC(I)=C1 MWHJEWBLTYDUKD-UHFFFAOYSA-N 0.000 abstract 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 abstract 2
- VWAPODDPPKUMAW-UHFFFAOYSA-N 4-methyl-2-propoxythiophene Chemical compound CCCOC1=CC(C)=CS1 VWAPODDPPKUMAW-UHFFFAOYSA-N 0.000 abstract 2
- 239000002585 base Substances 0.000 abstract 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 abstract 1
- 238000010751 Ullmann type reaction Methods 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000005826 halohydrocarbons Chemical class 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 230000026045 iodination Effects 0.000 abstract 1
- 238000006192 iodination reaction Methods 0.000 abstract 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 1
- 238000005096 rolling process Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Ester de 2,5-pirrolidin-1-ilo de ácido 4-bromo-3-metil-5-propoxitiofen-2-carboxílico y a su intermedio el éster de 2,5-pirrolidin-1-ilo de ácido 3-metil-5-propoxitiofen-2-carboxílico. Síntesis regioespecífica del éster de 2,-dioxo-pirrolidin-1-ilode ácido 4-bromo-3-metil-5-propoxitiofen-2-carboxíllico, que comprende las etapas de yodacion de 3-metil-tiofeno con un agente rodante en presencia de una base fuerte en un disolvente polar aprotico o hidrocarbonato para dar lugar a 2-yodo-4-metiltiofeno; condensacion de Ullmann de 2-yodo-4-metiltiofeno con una sal de propoxido de metal alcalino usando un catalizador de cobre en propanol para producir 4-metil-2-propoxitiofeno; condensacion del 4-metil-2-propoxitiofeno con CO2 usando unabase fuerte en un disolvente polar aprotico o hidrocarbonato para producir ácido 3-metil-5-propoxi-tiofen-2-carboxílico; esterificacion del ácido 3-metil-5-propoxi-tiofen-2-carboxílico con N-hidroxisuccinimida en presencia de un agente decondensacion en un disolvente polar aprotico, hidrocarbonato o halohidrocarbonado para producir éster de 2,5-dioxo-pirrolidin-1-ilo de ácido 3 -metil-5-propoxitiofen-2-carboxílico; y brotacion del éster de 2,5-dioxo-pirrolidin-1-ilo de ácido 3-metil-5-propoxitiofen-2-carboxílico con un agente de bromacion en un disolvente inerte para producir éster de 2,5-dioxo-pirrolidin-1-ilo de ácido 4-bromo-3-metil-5-propoxitiofen-2-carboxílico.2,5-Pyrrolidin-1-yl ester of 4-bromo-3-methyl-5-propoxythiophene-2-carboxylic acid and in its intermediate the 2,5-pyrrolidin-1-yl ester of 3-methyl-5 acid -propoxythiophene-2-carboxylic. Regiospecific synthesis of the ester of 2, -dioxo-pyrrolidin-1-ylde 4-bromo-3-methyl-5-propoxythiophene-2-carboxylic acid, comprising the steps of iodination of 3-methyl-thiophene with a rolling agent in the presence of a strong base in an aprotic polar solvent or hydrocarbonate to give rise to 2-iodo-4-methylthiophene; Ullmann condensation of 2-iodo-4-methylthiophene with an alkali metal propoxide salt using a copper catalyst in propanol to produce 4-methyl-2-propoxythiophene; condensation of 4-methyl-2-propoxythiophene with CO2 using a strong base in an aprotic polar solvent or hydrocarbonate to produce 3-methyl-5-propoxy-thiophene-2-carboxylic acid; esterification of 3-methyl-5-propoxy-thiophene-2-carboxylic acid with N-hydroxysuccinimide in the presence of a condensing agent in an aprotic polar solvent, hydrocarbonate or halohydrocarbon to produce 2,5-dioxo-pyrrolidin-1-yl ester of 3-methyl-5-propoxythiophene-2-carboxylic acid; and sprouting of the 2,5-dioxo-pyrrolidin-1-yl ester of 3-methyl-5-propoxythiophene-2-carboxylic acid with a brominating agent in an inert solvent to produce 2,5-dioxo-pyrrolidine- ester 1-yl of 4-bromo-3-methyl-5-propoxythiophene-2-carboxylic acid.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US90883907P | 2007-03-29 | 2007-03-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR065859A1 true AR065859A1 (en) | 2009-07-08 |
Family
ID=39530622
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP080101261A AR065859A1 (en) | 2007-03-29 | 2008-03-27 | ESTER OF 2,5-DIOXO-PIRROLIDIN-1-ILO OF ACID 4-BROMO-3-METIL-5-PROPOXITIOFEN-2- CARBOXILICO, ITS REGIO-SPECIFIC SYNTHESIS AND AN INTERMEDIATE OF THE SAME |
Country Status (3)
| Country | Link |
|---|---|
| AR (1) | AR065859A1 (en) |
| TW (1) | TW200904810A (en) |
| WO (1) | WO2008121669A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HRP20151338T1 (en) * | 2008-08-22 | 2016-01-15 | Sanofi | [4- (5-AMINOMETHYL-2-FLUORO-PHENYL) -PIPERIDIN-1-IL] - [7-FLUORO-1- (2-METHOXY-ETHYL) -4TRIFLUOROMETOXY-1H-INDOL-3-IL] METHANONE AS INHIBITOR MASTOCYT TRIPTASES |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DOP2005000039A (en) * | 2004-03-26 | 2005-10-31 | Aventis Pharma Inc | HYDROCHLORIDE OF [4- (5-AMINOMETIL-2-FLUORO-PHENYL) - PIPERIDIN-1-IL] - (4-BOMO-3-METHYL-5-PROPOXI-TIOFEN-2-IL) -METANONE AS AN INHIBITOR OF THE MASTOCYT TRIPTASE |
-
2008
- 2008-03-27 WO PCT/US2008/058346 patent/WO2008121669A1/en not_active Ceased
- 2008-03-27 AR ARP080101261A patent/AR065859A1/en not_active Application Discontinuation
- 2008-03-28 TW TW097111151A patent/TW200904810A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TW200904810A (en) | 2009-02-01 |
| WO2008121669A1 (en) | 2008-10-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA | Abandonment or withdrawal |