专利号:WO-2025115036-A1 优先权日:2023-11-29 标题:A process for the synthesis of 2-(4-chlorophenyl)-2-hydroxy-n-(3-methoxy-4-(prop-2- yn-1-yloxy)phenethyl)acetamide, a key intermediate of mandipropamid 发明人:DEB INDUBHUSAN; MONDAL IMTIAJ; NASKAR KOUSHIK; ROY SHANTONU 权利人:COUNCIL SCIENT IND RES 摘要:The present invention provides an improved method for the preparation of building blocks 2- (4-chlorophenyl)-2-hydroxy-N-(3-methoxy-4-(prop-2-yn-1-yloxy)phenethyl)acetamide, a key intermediate for the synthesis of Mandipropamid. An efficient, safe, cost-effective method for the preparation of Mandipropamid is developed. The method involves simple Nitro-aldol reaction, LAH reduction and mild Amidation reaction for synthesizing key intermediate 2-(4- chlorophenyl)-2-hydroxy-N-(3-methoxy-4-(prop-2-yn-1-yloxy)phenethyl)acetamide (E). The current synthesis method of the invention has relatively simple operation, mild reaction conditions, high yield and a simple process with, a yield up to 90%. Subsequent product purification of this method uses filtration and crystallization methods and easy column chromatography separation. This approach is highly effective and scalable, contributing to both atom and step economy in the process Therefore, the research of its synthetic process has a wide range of applications from the drug development and material synthesis point of view.
专利号:US-8129560-B2 优先权日:2005-08-15 标 题 :Process for the synthesis of mandipropamid and derivatives thereof 发明人:BOWDEN MARTIN CHARLES; CLARK THOMAS AITCHESON; GIORDANO FANNY; JAU BEAT; SCHNEIDER HANS-DIETER; SEIFERT GOTTFRIED; ZELLER MARTIN; FABER DOMINIK; WISS JUERG 权利人:BOWDEN MARTIN CHARLES; CLARK THOMAS AITCHESON; GIORDANO FANNY; JAU BEAT; SCHNEIDER HANS-DIETER; SEIFERT GOTTFRIED; ZELLER MARTIN; FABER DOMINIK; WISS JUERG; SYNGENTA CROP PROT INC 摘要:A process for the preparation of a compound of formula (I), the process comprising: (i) the reaction of a compound of formula (III), with a compound of formula (IV) to give a compound of formula (II), and (ii) the reaction of the compound of formula (II) with a leaving group, to give the compound of formula (I).
专利号:WO-2025056767-A1 优先权日:2023-09-15 标题 :Process for the preparation of enantiomerically enriched aliphatic amines 发明人:BOU HAMDAN FARHAN; GODINEAU EDOUARD; SMEJKAL TOMAS; DUMEUNIER RAPHAEL; BOUSSEMGHOUNE MOHAMED ABDELOUAHAB; BLUM MATHIAS 权利人:SYNGENTA CROP PROTECTION AG 摘要:The present invention relates to a process for the preparation of enantiomerically enriched cyclobutylamines of formula (I) from α-tertiary cyclobutanones and reacting said enantiomerically enriched cyclobutylamines to enantiomerically enriched cyclobutylamides. Such compounds are useful intermediates in the synthesis of microbiocidal thiazole compounds.
专利号:US-2016073631-A1 优先权日:2013-03-04 标 题 :Process for the preparation of dihydropyrrole derivatives 发明人:EL QACEMI MYRIEM; SMITS HELMARS; CASSAYRE JEROME YVES; MULHOLLAND NICHOLAS PHILLIP; RENOLD PETER; GODINEAU EDOUARD; PITTERNA THOMAS 权利人:SYNGENTA PARTICIPATIONS AG; SYNGENTA LTD 摘要:The present invention provides stereoselective processes for the preparation of compounds of formula (I) n n n n n n n n n n n n wherein n P is phenyl, naphthyl, a 6-membered heteroaryl group containing one or two nitrogen atoms as ring members, or a 10-membered bicyclic heteroaryl group containing one or two nitrogen atoms as ring members, and wherein the phenyl, naphthyl and heteroaryl groups are optionally substituted; n R 1 is chlorodifluoromethyl or trifluoromethyl; n R 2 is optionally substituted aryl or optionally substituted heteroaryl; n n is 0 or 1; n including the process comprising n (a-i) reacting a compound of formula II n n n n n n n n n n n n n n n n wherein P, R 1 and R 2 are as defined for the compound of formula I; n with nitromethane in the presence a chiral catalyst to give a compound of formula III n n n n n n n n n n n n n n n n wherein P, R 1 and R 2 are as defined for the compound of formula I; and n (a-ii) reductively cyclising the compound of formula III to give the compound of formula I. n n n n n The invention also provides intermediates useful for processes for the synthesis of compounds of formula (I).
专利号:US-9233920-B2 优先权日:2010-06-11 标题 :Process for the preparation of dihydropyrrole derivatives 发明人:EL QACEMI MYRIEM; SMITS HELMARS; CASSAYRE JEROME YVES; MULHOLLAND NICHOLAS PHILLIP; RENOLD PETER; GODINEAU EDOUARD; PITTERNA THOMAS 权利人:EL QACEMI MYRIEM; SMITS HELMARS; CASSAYRE JEROME YVES; MULHOLLAND NICHOLAS PHILLIP; RENOLD PETER; GODINEAU EDOUARD; PITTERNA THOMAS; SYNGENTA PARTICIPATIONS AG; SYNGENTA LTD 摘要:The present invention provides stereoselective processes for the preparation of compounds of formula (I) wherein P is phenyl, naphthyl, a 6-membered heteroaryl group containing one or two nitrogen atoms as ring members, or a 10-membered bicyclic heteroaryl group containing one or two nitrogen atoms as ring members, and wherein the phenyl, naphthyl and heteroaryl groups are optionally substituted; R 1 is chlorodifluoromethyl or trifluoromethyl; R 2 is optionally substituted aryl or optionally substituted heteroaryl; n is 0 or 1; including the process comprising (a-i) reacting a compound of formula II wherein P, R 1 and R 2 are as defined for the compound of formula I; with nitromethane in the presence a chiral catalyst to give a compound of formula III Wherein P, R 1 and R 2 are as defined for the compound of formula I; and (a-ii) reductively cyclizing the compound of formula III to give the compound of formula I. The invention also provides intermediates useful for processes for the synthesis of compounds of formula (I).
专利号:US-10906880-B2 优先权日:2016-01-26 标题:Kind of isothiazole oxime ether-containing strobilurin derivatives and its preparation methods and application 发明人:FAN ZHIJIN; CHEN LAI; GUO XIAOFENG; ZHU YUJIE; QIAN XIAOLIN; MA LIUYONG; ZHANG NAILOU; WANG HAIXIA; ZHANG ZHIMING; XU JINGHUA; SONG YINQI 权利人:UNIV NANKAI 摘要:The present invention is that provided a synthesis method of a series of isothiazole oxime ether containing strobilurin derivatives IV. The present invention relates to 3,4-dichloroisothiazolyl oxime ether strobilurin derivatives, and their chemical structural formula is as shown by IV. n n n n n n n n n n The invention discloses the structural formula of the above compound, the synthesis method and the use as an insecticide, a fungicide, an anti-plant virus agent, and an agriculturally acceptable auxiliary or synergist and a commercial insecticide. The use of a fungicide, an anti-plant virus agent and an acaricide in combination for controlling agricultural, forestry, horticultural plant pests, diseases, virus diseases and preparation methods.
1: Ziegler MJ, Yserentant K, Dunsing V, Middel V, Gralak AJ, Pakari K, Bargstedt J, Kern C, Petrich A, Chiantia S, Strähle U, Herten DP, Wombacher R. Mandipropamid as a chemical inducer of proximity for in vivo applications. Nat Chem Biol. 2022 Jan;18(1):64-69. doi: 10.1038/s41589-021-00922-3. Epub 2021 Dec 21. 2: Hou Z, Hou X, Wei L, Cao Z, Lu Z, Liu H, Lu Z. Degradation and residues of mandipropamid in soil and ginseng and dietary risk assessment in Chinese culture. Environ Sci Pollut Res Int. 2023 Feb;30(10):26367-26374. doi: 10.1007/s11356-022-24024-2. Epub 2022 Nov 11. 29(40):60244-60258. doi: 10.1007/s11356-022-20202-4. Epub 2022 Apr 13. 27(32):40148-40155. doi: 10.1007/s11356-020-10061-2. Epub 2020 Jul 13. Bellisai G, Bernasconi G, Brancato A, Carrasco Cabrera L, Castellan I, Del Aguila M, Ferreira L, Santonja GG, Greco L, Jarrah S, Leuschner R, Magrans JO, Miron I, Nave S, Pedersen R, Reich H, Robinson T, Ruocco S, Santos M, Scarlato AP, Theobald A, Verani A. Setting of import tolerances for mandipropamid in papayas. EFSA J. 2023 Jan 11;21(1):e07741. doi: 10.2903/j.efsa.2023.7741. 6: Mu S, Dou L, Ye Y, Chi D, Zhang K. Effects of Household Processing on Residues of the Chiral Fungicide Mandipropamid in Four Common Vegetables. Int J Environ Res Public Health. 2022 Nov 23;19(23):15543. doi: 10.3390/ijerph192315543.
合成参考文献
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