HRP20160001T1 - Postupak za pripravu fenil supstituiranih n-metoksi-[1-metil-2-feniletil]amida 3-difluorometil-1-metil-1h-pirazol-4-karboksilne kiseline - Google Patents
Postupak za pripravu fenil supstituiranih n-metoksi-[1-metil-2-feniletil]amida 3-difluorometil-1-metil-1h-pirazol-4-karboksilne kiseline Download PDFInfo
- Publication number
- HRP20160001T1 HRP20160001T1 HRP20160001TT HRP20160001T HRP20160001T1 HR P20160001 T1 HRP20160001 T1 HR P20160001T1 HR P20160001T T HRP20160001T T HR P20160001TT HR P20160001 T HRP20160001 T HR P20160001T HR P20160001 T1 HRP20160001 T1 HR P20160001T1
- Authority
- HR
- Croatia
- Prior art keywords
- formula
- compound
- methyl
- preparation
- image
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 7
- XKDRDLNBSRCAGQ-UHFFFAOYSA-N 3-(difluoromethyl)-n-methoxy-1-methyl-n-(1-phenylpropan-2-yl)pyrazole-4-carboxamide Chemical class C=1N(C)N=C(C(F)F)C=1C(=O)N(OC)C(C)CC1=CC=CC=C1 XKDRDLNBSRCAGQ-UHFFFAOYSA-N 0.000 title 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 13
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 239000003960 organic solvent Substances 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims 1
- 125000006765 (C2-C6) haloalkenyloxy group Chemical group 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 claims 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Claims (5)
1. Postupak za pripremanje spoja s formulom I
[image]
naznačen time
R1 je vodik, halogen ili C1-C6alkil;
R2 je vodik, halogen, C1-C6alkil, C2-C6alkenil, C3-C6alkinil, C3-C6cikloalkil-C3-C6alkinil, halofenoksi, halofenil-C3-C6alkinil, C(C1-C4alkil)=NO-C1-C4alkil, C1-C6haloalkil, C1-C6haloalkoksi, C2-C6haloalkenil ili C2-C6haloalkeniloksi; i
R3 je vodik, halogen ili C1-C6alkil;
te navedeni postupak obuhvaća
a) dodavanje spoja s formulom II
[image]
pri čemu R1, R2 i R3 imaju značenja kao što je opisano pod formulom I, u prisutnosti inertnog organskog otapala u smjesu koja sadrži organski nitrit s formulom III
R4-O-N=O (III),
pri čemu R4 je C1-C8alkil, spoja s formulom IV
[image]
u inertno organsko otapalo;
b) reakciju nastalog spoja formule V
[image]
pri čemu R1, R2 i R3 imaju značenja kao što je opisano pod formulom I sa O-metilhidroksilaminom s formulom VI
H2N-O-CH3 (VI),
u spoj s formulom VII
[image]
pri čemu R1, R2 i R3 imaju značenja kao što je opisano pod formulom I;
c) redukciju spoja s formulom VII u spoj s formulom VIII
[image]
pri čemu R1, R2 i R3 imaju značenja kao što je opisano pod formulom I
d) i reakciju spoja s formulom VIII sa spojem s formulom IX
[image]
u kojoj R* je halogen, hidroksi ili C1-6 alkoksi u spoj s formulom I.
2. Postupak prema zahtjevu 1 za pripremanje spoja s formulom I, naznačen time da je barem jedan od R1, R2 i R3 različit od vodika.
3. Postupak prema zahtjevu 1 za pripremanje spoja s formulom I, naznačen time da barem jedan od R1, R2 i R3 je halogen.
4. Postupak prema zahtjevu 1 za pripremanje spoja s formulom I, naznačen time da R1, R2 i R3 su kloro.
5. Postupak prema zahtjevu 1 za pripremanje spoja s formulom I, naznačen time da R4 je C4-C7alkil.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12157354 | 2012-02-28 | ||
| EP13705816.0A EP2819997B1 (en) | 2012-02-28 | 2013-02-26 | Process for the preparation of phenyl substituted 3 - difluoromethyl - 1 -methyl - 1h - pyrazole - 4 - carboxylic acid n-methoxy- [1 -methyl- 2 - phenylethyl]amides |
| PCT/EP2013/053773 WO2013127764A1 (en) | 2012-02-28 | 2013-02-26 | Process for the preparation of phenyl substituted 3 - difluoromethyl - 1 -methyl - 1h - pyrazole - 4 - carboxylic n-methoxy- [1 -methyl- 2 - phenylethyl] amides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20160001T1 true HRP20160001T1 (hr) | 2016-02-12 |
Family
ID=47748653
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20160001TT HRP20160001T1 (hr) | 2012-02-28 | 2015-12-31 | Postupak za pripravu fenil supstituiranih n-metoksi-[1-metil-2-feniletil]amida 3-difluorometil-1-metil-1h-pirazol-4-karboksilne kiseline |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US9051272B2 (hr) |
| EP (1) | EP2819997B1 (hr) |
| JP (1) | JP6078563B2 (hr) |
| KR (1) | KR102031809B1 (hr) |
| CN (1) | CN104144914B (hr) |
| AR (1) | AR090172A1 (hr) |
| AU (1) | AU2013225123B2 (hr) |
| BR (1) | BR112014020556B1 (hr) |
| CA (1) | CA2863467C (hr) |
| CO (1) | CO7051031A2 (hr) |
| DK (1) | DK2819997T3 (hr) |
| ES (1) | ES2558586T3 (hr) |
| HR (1) | HRP20160001T1 (hr) |
| HU (1) | HUE026564T2 (hr) |
| IL (1) | IL233937A (hr) |
| MX (1) | MX347564B (hr) |
| PL (1) | PL2819997T3 (hr) |
| TW (1) | TWI491594B (hr) |
| WO (1) | WO2013127764A1 (hr) |
| ZA (1) | ZA201405823B (hr) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10130095B2 (en) | 2014-02-19 | 2018-11-20 | BASF Agro B.V. | Fungicidal compositions of pyrazolecarboxylic acid alkoxyamides |
| WO2016174042A1 (en) | 2015-04-27 | 2016-11-03 | BASF Agro B.V. | Pesticidal compositions |
| WO2017207368A1 (en) | 2016-06-02 | 2017-12-07 | BASF Agro B.V. | Fungicidal compositions |
| CN108610290B (zh) * | 2018-06-11 | 2020-04-24 | 武汉工程大学 | 一种氟唑菌酰羟胺的制备方法 |
| GB201818113D0 (en) * | 2018-11-06 | 2018-12-19 | Syngenta Participations Ag | Process |
| GB201818117D0 (en) * | 2018-11-06 | 2018-12-19 | Syngenta Participations Ag | Enantioselective process |
| GB201821036D0 (en) | 2018-12-21 | 2019-02-06 | Syngenta Participations Ag | Nematicidal compositions |
| AU2022210374A1 (en) | 2021-01-22 | 2023-07-13 | Syngenta Crop Protection Ag | Method for the control or suppression of phytopathogenic bacteria |
| CN115703701B (zh) * | 2021-08-16 | 2024-06-25 | 上海晓明检测技术服务有限公司 | 一种微通道连续合成1-(2,4,6-三氯-苯基)-丙-2-酮的方法 |
| TW202412626A (zh) | 2022-08-16 | 2024-04-01 | 瑞士商先正達農作物保護股份公司 | 新用途 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1298349B1 (it) * | 1996-05-29 | 2000-01-05 | Alfa Chem Ital | Processo per la produzione di 1 - (3-trifluorometil) fenil-propan- 2-one intermedio nella sintesi della fenfluramina |
| WO2000034229A1 (en) * | 1998-12-10 | 2000-06-15 | Bayer Aktiengesellschaft | Process for the preparation of strobilurin intermediates |
| JP2008533033A (ja) * | 2005-03-10 | 2008-08-21 | メルク エンド カムパニー インコーポレーテッド | 抗糖尿病化合物の新規な結晶形態 |
| MY152114A (en) * | 2008-12-05 | 2014-08-15 | Syngenta Participations Ag | Novel pyrazole-4-n-alkoxycarboxamides as microbiocides |
| EP2592931A4 (en) * | 2010-07-13 | 2013-12-11 | Syngenta Participations Ag | SAFENER COMPOSITIONS AND METHOD FOR REDUCING MYCOTOXINES |
-
2013
- 2013-02-26 TW TW102106650A patent/TWI491594B/zh active
- 2013-02-26 MX MX2014009948A patent/MX347564B/es active IP Right Grant
- 2013-02-26 DK DK13705816.0T patent/DK2819997T3/en active
- 2013-02-26 EP EP13705816.0A patent/EP2819997B1/en active Active
- 2013-02-26 HU HUE13705816A patent/HUE026564T2/hu unknown
- 2013-02-26 PL PL13705816T patent/PL2819997T3/pl unknown
- 2013-02-26 WO PCT/EP2013/053773 patent/WO2013127764A1/en active Application Filing
- 2013-02-26 BR BR112014020556A patent/BR112014020556B1/pt active IP Right Grant
- 2013-02-26 KR KR1020147024947A patent/KR102031809B1/ko active IP Right Grant
- 2013-02-26 AU AU2013225123A patent/AU2013225123B2/en active Active
- 2013-02-26 JP JP2014559177A patent/JP6078563B2/ja active Active
- 2013-02-26 CA CA2863467A patent/CA2863467C/en active Active
- 2013-02-26 ES ES13705816.0T patent/ES2558586T3/es active Active
- 2013-02-26 US US14/374,547 patent/US9051272B2/en active Active
- 2013-02-26 CN CN201380011368.1A patent/CN104144914B/zh active Active
- 2013-02-27 AR ARP130100601A patent/AR090172A1/es active IP Right Grant
-
2014
- 2014-08-04 IL IL233937A patent/IL233937A/en active IP Right Grant
- 2014-08-07 ZA ZA2014/05823A patent/ZA201405823B/en unknown
- 2014-08-26 CO CO14187079A patent/CO7051031A2/es unknown
-
2015
- 2015-12-31 HR HRP20160001TT patent/HRP20160001T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP6078563B2 (ja) | 2017-02-08 |
| WO2013127764A1 (en) | 2013-09-06 |
| HUE026564T2 (hu) | 2016-06-28 |
| MX2014009948A (es) | 2014-11-12 |
| TW201348209A (zh) | 2013-12-01 |
| CO7051031A2 (es) | 2014-09-10 |
| CA2863467C (en) | 2020-03-10 |
| ES2558586T3 (es) | 2016-02-05 |
| US20150018562A1 (en) | 2015-01-15 |
| BR112014020556B1 (pt) | 2019-11-26 |
| CN104144914B (zh) | 2016-03-02 |
| DK2819997T3 (en) | 2016-01-18 |
| CA2863467A1 (en) | 2013-09-06 |
| KR20140138154A (ko) | 2014-12-03 |
| KR102031809B1 (ko) | 2019-10-14 |
| JP2015508794A (ja) | 2015-03-23 |
| AU2013225123B2 (en) | 2016-10-20 |
| TWI491594B (zh) | 2015-07-11 |
| AR090172A1 (es) | 2014-10-22 |
| IL233937A0 (en) | 2014-09-30 |
| ZA201405823B (en) | 2015-11-25 |
| EP2819997A1 (en) | 2015-01-07 |
| EP2819997B1 (en) | 2015-10-28 |
| IL233937A (en) | 2016-04-21 |
| CN104144914A (zh) | 2014-11-12 |
| PL2819997T3 (pl) | 2016-03-31 |
| MX347564B (es) | 2017-05-03 |
| US9051272B2 (en) | 2015-06-09 |
| AU2013225123A1 (en) | 2014-09-18 |
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