JP2014511367A5 - - Google Patents
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- Publication number
- JP2014511367A5 JP2014511367A5 JP2013551371A JP2013551371A JP2014511367A5 JP 2014511367 A5 JP2014511367 A5 JP 2014511367A5 JP 2013551371 A JP2013551371 A JP 2013551371A JP 2013551371 A JP2013551371 A JP 2013551371A JP 2014511367 A5 JP2014511367 A5 JP 2014511367A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- alkyl
- cycloalkyl
- cyano
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 10
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000006450 cyclopropyl cyclopropyl group Chemical group 0.000 claims description 7
- 239000003446 ligand Substances 0.000 claims description 7
- 229910052763 palladium Inorganic materials 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 6
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 4
- -1 hydroxypropyl Chemical group 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 238000005576 amination reaction Methods 0.000 claims description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- BCJVBDBJSMFBRW-UHFFFAOYSA-N 4-diphenylphosphanylbutyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCCP(C=1C=CC=CC=1)C1=CC=CC=C1 BCJVBDBJSMFBRW-UHFFFAOYSA-N 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 0 *c(cc1*)cc(*)c1N Chemical compound *c(cc1*)cc(*)c1N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical group [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161437280P | 2011-01-28 | 2011-01-28 | |
| US61/437,280 | 2011-01-28 | ||
| PCT/US2012/022899 WO2012103436A1 (en) | 2011-01-28 | 2012-01-27 | Method for preparing 2-aminobenzamide derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2014511367A JP2014511367A (ja) | 2014-05-15 |
| JP2014511367A5 true JP2014511367A5 (enExample) | 2015-03-05 |
Family
ID=45582051
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013551371A Pending JP2014511367A (ja) | 2011-01-28 | 2012-01-27 | ２−アミノベンズアミド誘導体の調製方法 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US8871939B2 (enExample) |
| EP (1) | EP2668153B1 (enExample) |
| JP (1) | JP2014511367A (enExample) |
| KR (1) | KR20140006007A (enExample) |
| CN (1) | CN103328434A (enExample) |
| AU (1) | AU2012211165A1 (enExample) |
| BR (1) | BR112013018228A2 (enExample) |
| HU (1) | HUE025309T2 (enExample) |
| IL (1) | IL226892A (enExample) |
| MX (1) | MX2013008560A (enExample) |
| TW (1) | TW201235338A (enExample) |
| WO (1) | WO2012103436A1 (enExample) |
| ZA (1) | ZA201304330B (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107365263A (zh) * | 2011-07-08 | 2017-11-21 | 拜耳知识产权有限责任公司 | 制备2‑氨基‑5‑氰基‑n,3‑二甲基苯甲酰胺的方法 |
| TWI644888B (zh) | 2012-02-07 | 2018-12-21 | 拜耳智慧財產有限公司 | 用於製備經取代之鄰胺苯甲酸衍生物之方法 |
| TWI678354B (zh) * | 2014-05-29 | 2019-12-01 | 新加坡商艾佛艾姆希農業新加坡有限公司 | 藉空氣氧化製備３-甲基-２-硝基苯甲酸之製程 |
| CN107522689B (zh) * | 2016-06-21 | 2021-11-23 | 华东理工大学 | 氯虫苯甲酰胺的多晶型及其制备方法 |
| US12234217B2 (en) * | 2018-12-03 | 2025-02-25 | Fmc Corporation | Method for preparing N-phenylpyrazole-1-carboxamides |
| EP3902792B1 (en) * | 2018-12-24 | 2025-05-21 | UPL Ltd | Process for preparation of anthranilamides |
| HUE069962T2 (hu) | 2019-02-18 | 2025-04-28 | Pi Industries Ltd | Eljárás antranil-diamidok és intermedierjeik elõállítására |
| KR102841700B1 (ko) | 2019-02-22 | 2025-08-01 | 피아이 인더스트리스 엘티디. | 안트라닐산 디아미드 화합물 및 그의 중간체의 합성 방법 |
| CN115315419A (zh) * | 2020-04-29 | 2022-11-08 | 巴斯夫欧洲公司 | 通过钯催化的羰基化反应制备芳族羧酰胺 |
| TW202219046A (zh) * | 2020-07-23 | 2022-05-16 | 美商富曼西公司 | 藉由使用一結晶中間體改善剋安勃製程 |
| US20230339844A1 (en) | 2020-09-17 | 2023-10-26 | Pi Industries Ltd. | A process for the synthesis of anthranilic acid/amide compounds and intermediates thereof |
| TW202222162A (zh) | 2020-09-26 | 2022-06-16 | 印度商皮埃企業有限公司 | 鄰胺苯甲酸／醯胺化合物及其中間體的合成方法 |
| CN115417781B (zh) * | 2022-09-30 | 2023-08-29 | 西安凯立新材料股份有限公司 | 一种制备氯虫苯甲酰胺中间体k胺的方法 |
| WO2024116197A1 (en) * | 2022-11-30 | 2024-06-06 | Natco Pharma Limited | An improved process for the preparation of intermediate of cyantraniliprole |
| AU2024286996A1 (en) * | 2023-06-08 | 2026-01-08 | Jiangsu Hengrui Pharmaceuticals Co., Ltd. | Preparation method for formamide compounds |
| WO2025134143A1 (en) | 2023-12-19 | 2025-06-26 | Pi Industries Ltd. | A method for the synthesis of substituted anthranilic amide compounds, intermediates and salts thereof |
| WO2025188963A1 (en) | 2024-03-06 | 2025-09-12 | Fmc Corporation | Metal catalyzed synthesis of 2-aminobenzamide derivatives |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI371450B (en) | 2001-08-13 | 2012-09-01 | Du Pont | Novel substituted dihydro 3-halo-1h-pyrazole-5-carboxylates,their preparation and use |
| AR036872A1 (es) | 2001-08-13 | 2004-10-13 | Du Pont | Compuesto de antranilamida, composicion que lo comprende y metodo para controlar una plaga de invertebrados |
| CA2454298A1 (en) | 2001-08-13 | 2003-02-27 | Gary David Annis | Substituted 1h-dihydropyrazoles, their preparation and use |
| ATE417829T1 (de) * | 2001-08-16 | 2009-01-15 | Du Pont | Substituierte anthranilamide und ihre verwendung als pesticide |
| JP2004043474A (ja) | 2002-07-05 | 2004-02-12 | Nippon Nohyaku Co Ltd | ２−アミノ安息香酸誘導体及びその製造方法 |
| TWI343376B (en) | 2002-07-31 | 2011-06-11 | Du Pont | Method for preparing 3-halo-4, 5-dihydro-1h-pyrazoles |
| SE526014C2 (sv) | 2002-09-11 | 2005-06-14 | Anmedic Ab | En apparat för att försörja en patient med en blandning av bärgas och ett gasformigt anestesimedel |
| US7211270B2 (en) * | 2002-10-04 | 2007-05-01 | E. I. Du Pont De Nemours And Company | Anthranilamide insecticides |
| TWI367882B (en) | 2003-03-26 | 2012-07-11 | Du Pont | Preparation and use of 2-substituted-5-oxo-3-pyrazolidinecarboxylates |
| JP4775259B2 (ja) * | 2004-03-31 | 2011-09-21 | 味の素株式会社 | アニリン誘導体 |
| TWI363756B (en) | 2004-12-07 | 2012-05-11 | Du Pont | Method for preparing n-phenylpyrazole-1-carboxamides |
| GB0426894D0 (en) | 2004-12-08 | 2005-01-12 | Stylacats Ltd | Process |
| US20100056515A1 (en) | 2006-10-25 | 2010-03-04 | Kazuyoshi Aso | Benzimidazole compounds |
| TWI431000B (zh) * | 2008-03-05 | 2014-03-21 | Du Pont | 製備２－胺基－５－氰基苯甲酸衍生物之方法 |
| JP5619730B2 (ja) * | 2008-05-27 | 2014-11-05 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 芳香族およびヘテロ芳香族カルボン酸、カルボン酸エステルおよびカルボン酸アミドの製造方法 |
| WO2010093191A2 (en) | 2009-02-13 | 2010-08-19 | Lg Life Sciences Ltd. | Novel compounds effective as xanthine oxidase inhibitors, method for preparing the same, and pharmaceutical composition containing the same |
| CN101717395A (zh) * | 2009-12-04 | 2010-06-02 | 南开大学 | 一种氯虫苯甲酰胺农药的合成方法 |
-
2012
- 2012-01-27 EP EP12703656.4A patent/EP2668153B1/en not_active Not-in-force
- 2012-01-27 WO PCT/US2012/022899 patent/WO2012103436A1/en not_active Ceased
- 2012-01-27 CN CN2012800057831A patent/CN103328434A/zh active Pending
- 2012-01-27 KR KR1020137022651A patent/KR20140006007A/ko not_active Withdrawn
- 2012-01-27 AU AU2012211165A patent/AU2012211165A1/en not_active Abandoned
- 2012-01-27 JP JP2013551371A patent/JP2014511367A/ja active Pending
- 2012-01-27 HU HUE12703656A patent/HUE025309T2/en unknown
- 2012-01-27 MX MX2013008560A patent/MX2013008560A/es not_active Application Discontinuation
- 2012-01-27 BR BR112013018228A patent/BR112013018228A2/pt not_active IP Right Cessation
- 2012-01-27 US US13/981,919 patent/US8871939B2/en active Active - Reinstated
- 2012-01-30 TW TW101102830A patent/TW201235338A/zh unknown
-
2013
- 2013-06-12 IL IL226892A patent/IL226892A/en not_active IP Right Cessation
- 2013-06-12 ZA ZA2013/04330A patent/ZA201304330B/en unknown
-
2014
- 2014-09-16 US US14/487,600 patent/US9162973B2/en active Active
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