WO2022012963A1 - 4-furanamide und verfahren zu deren herstellung - Google Patents
4-furanamide und verfahren zu deren herstellung Download PDFInfo
- Publication number
- WO2022012963A1 WO2022012963A1 PCT/EP2021/068287 EP2021068287W WO2022012963A1 WO 2022012963 A1 WO2022012963 A1 WO 2022012963A1 EP 2021068287 W EP2021068287 W EP 2021068287W WO 2022012963 A1 WO2022012963 A1 WO 2022012963A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compounds
- general formula
- iii
- reaction
- furanamides
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Definitions
- the present invention relates to 4-furanamides of the general formula (I) and a process for the preparation of these compounds and their use as important precursors for the synthesis of agrochemical and pharmaceutical active ingredients.
- 4-Furanamides of the general formula (I) are important precursors of agrochemical (cf. WO2018/228985) and pharmaceutical active ingredients (e.g. Craig et al. Bioorganic & Medicinal Chemistry Fetters, 12(18), 2647-2650; 2002).
- 4-Furanamides of the general formula (I) serve as starting material for the production of tetrahydro- and dihydrofuran carboxylic acids - and esters.
- the compounds of the general formula (I) are not known to date, but they can serve as important building blocks for the synthesis of agrochemical and pharmaceutical active ingredients. Accordingly, the synthesis of the compounds of the general formula (I) has not been described hitherto.
- the analogous synthesis by F. Brucoli et al. has the disadvantage that it has a long reaction time and a relatively low yield.
- the present invention has for its object to find a method for preparing the compounds mentioned, so that the Compounds of the general formula (I) can be obtained in higher yields, in high purity and in an environmentally friendly manner, so that important intermediates for the production of active substances can be produced on an industrial scale.
- R 1 is COO(Ci-C 4 )-alkyl
- R 2 is CF 3 , CF 2 H, C2F5, CF2CI, CCh, characterized in that the compounds of general formula (II) wherein
- R 3 is halogen
- R 1 has the meanings given above in the presence of compounds of the general formula (III) R 2 CONH2, a Cu(I) salt, an amine, a base and ascorbic acid.
- R 1 represents COOCH3, COOC2H5, R 2 represents CF 3 , CF2H, R 3 represents Br, CI.
- radical definitions for the compounds of the general formulas (I), (II) and (III) are the following:
- R 1 represents COOCH3
- R 2 represents CF3
- R 3 stands for Br.
- Another object of the present invention are compounds of general formula (I)
- R 2 is CF 3, CF 2 H, C2F5, CF 2 Cl, is CCE.
- R1 is COOCH3, COOC2H5,
- R 2 is CF 3, CF 2 H.
- R 2 is CF 3.
- Alkali metal carbonates or trialkali metal phosphates are suitable as bases.
- Potassium carbonate is preferably used as the base.
- a copper(I) salt is used, preferably a copper(I) halide such as CuI or CuBr.
- CuBr is particularly preferred.
- the molar ratio of the compound of general formula (II) to compounds of general formula (III) is in the range from about 1:10 to 1:1, preferably 1:2 to 1:1, very particularly preferably 1:1.5 to 1:1.1.
- the reaction is usually carried out in a temperature range of 70-100°C.
- the reaction is preferably carried out at 80-90°C, very particularly preferably at 83-85°C.
- the reaction is usually carried out in a solvent, dioxane being preferred.
- vitamin C ascorbic acid
- heteroaromatic systems aromatic systems see Wang et al
- Cu(I)-catalyzed amidation with slightly different reaction conditions than in Wang et al.
- the filling opening is flushed with 90 ml of dry 1,4-dioxane.
- the vessel is sealed and nitrogen is passed through the stirred suspension for 15 minutes.
- the reaction mixture is heated to 83-85°C.
- a solution of 8.5 g (0.058 mol) of trans-N,N'-dimethylcyclohexane-1,2-diamine (97%) in 8.5 g of dry 1,4-dioxane is added.
- the mixture is then stirred at 83-85° C. for 3 hours.
- the mixture is then cooled to 15° C.
Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202180048847.5A CN115836060A (zh) | 2020-07-16 | 2021-07-02 | 4-呋喃酰胺及其制备方法 |
MX2023000727A MX2023000727A (es) | 2020-07-16 | 2021-07-02 | 4-furanamidas y procedimiento para su preparacion. |
KR1020237001395A KR20230040988A (ko) | 2020-07-16 | 2021-07-02 | 4-푸란아미드 및 그의 제조 방법 |
IL299857A IL299857A (en) | 2020-07-16 | 2021-07-02 | 4-furanamides and a method for their production |
US18/005,226 US20230265062A1 (en) | 2020-07-16 | 2021-07-02 | 4-furanamides and method for the production thereof |
BR112022026986A BR112022026986A2 (pt) | 2020-07-16 | 2021-07-02 | 4-furanamidas e método para preparação das mesmas |
EP21740006.8A EP4182306A1 (de) | 2020-07-16 | 2021-07-02 | 4-furanamide und verfahren zu deren herstellung |
JP2023502808A JP2023533838A (ja) | 2020-07-16 | 2021-07-02 | 4-フランアミドおよびその製造方法 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP20186138.2 | 2020-07-16 | ||
EP20186138 | 2020-07-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2022012963A1 true WO2022012963A1 (de) | 2022-01-20 |
Family
ID=71661673
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2021/068287 WO2022012963A1 (de) | 2020-07-16 | 2021-07-02 | 4-furanamide und verfahren zu deren herstellung |
Country Status (10)
Country | Link |
---|---|
US (1) | US20230265062A1 (de) |
EP (1) | EP4182306A1 (de) |
JP (1) | JP2023533838A (de) |
KR (1) | KR20230040988A (de) |
CN (1) | CN115836060A (de) |
BR (1) | BR112022026986A2 (de) |
IL (1) | IL299857A (de) |
MX (1) | MX2023000727A (de) |
TW (1) | TW202216673A (de) |
WO (1) | WO2022012963A1 (de) |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2018228985A1 (de) | 2017-06-13 | 2018-12-20 | Bayer Aktiengesellschaft | Herbizid wirksame 3-phenylisoxazolin-5-carboxamide von tetrahydro- und dihydrofurancarbonsäuren und -estern |
-
2021
- 2021-07-02 KR KR1020237001395A patent/KR20230040988A/ko unknown
- 2021-07-02 IL IL299857A patent/IL299857A/en unknown
- 2021-07-02 US US18/005,226 patent/US20230265062A1/en active Pending
- 2021-07-02 MX MX2023000727A patent/MX2023000727A/es unknown
- 2021-07-02 CN CN202180048847.5A patent/CN115836060A/zh active Pending
- 2021-07-02 JP JP2023502808A patent/JP2023533838A/ja active Pending
- 2021-07-02 BR BR112022026986A patent/BR112022026986A2/pt unknown
- 2021-07-02 EP EP21740006.8A patent/EP4182306A1/de active Pending
- 2021-07-02 WO PCT/EP2021/068287 patent/WO2022012963A1/de unknown
- 2021-07-14 TW TW110125806A patent/TW202216673A/zh unknown
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2018228985A1 (de) | 2017-06-13 | 2018-12-20 | Bayer Aktiengesellschaft | Herbizid wirksame 3-phenylisoxazolin-5-carboxamide von tetrahydro- und dihydrofurancarbonsäuren und -estern |
Non-Patent Citations (7)
Title |
---|
CRAIG ET AL., BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 12, no. 18, 2002, pages 2647 - 2650 |
CUILING WANG ET AL: "Synthesis of Imatinib by C-N Coupling Reaction of Primary Amide and Bromo-Substituted Pyrimidine Amine", ORGANIC PROCESS RESEARCH & DEVELOPMENT, vol. 23, no. 9, 20 September 2019 (2019-09-20), US, pages 1918 - 1925, XP055753518, ISSN: 1083-6160, DOI: 10.1021/acs.oprd.9b00227 * |
F. BRUCOLI ET AL., BIOORGANIC & MEDICINAL CHEMISTRY, vol. 20, no. 6, 2012, pages 2019 - 2024 |
FEDERICO BRUCOLI ET AL: "Efficient synthesis and biological evaluation of proximicins A, B and C", BIOORGANIC & MEDICINAL CHEMISTRY, ELSEVIER, NL, vol. 20, no. 6, 26 January 2012 (2012-01-26), pages 2019 - 2024, XP028465313, ISSN: 0968-0896, [retrieved on 20120204], DOI: 10.1016/J.BMC.2012.01.043 * |
JI ET AL., J. ORG. CHEM., vol. 77, 2012, pages 7471 |
SPEROTTO, DALTON TRANS., vol. 39, 2010, pages 10338 - 10351 |
WANG ET AL., ORG. PROCESS RES. DEV., vol. 23, 2019, pages 1918 |
Also Published As
Publication number | Publication date |
---|---|
IL299857A (en) | 2023-03-01 |
TW202216673A (zh) | 2022-05-01 |
CN115836060A (zh) | 2023-03-21 |
KR20230040988A (ko) | 2023-03-23 |
EP4182306A1 (de) | 2023-05-24 |
BR112022026986A2 (pt) | 2023-01-24 |
US20230265062A1 (en) | 2023-08-24 |
MX2023000727A (es) | 2023-02-13 |
JP2023533838A (ja) | 2023-08-04 |
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