title: Synthesis of highly substituted 5-(trifluoromethyl)ketoimidazoles using a mixed-solid/solution phase motif.
abstract: Using a combination of solid phase synthesis for the preparation of N-substituted-N-acylglycines 7 followed by solution-phase ring transformation of trifluoromethylacyl munchnone intermediate 8, a library of 200 trisubstituted-5-trifluoromethylketo (TFMK) imidazoles 9 was prepared. In a sublibrary, bromoacetate resin 4 was treated with 5 amines in parallel to give N-substituted glycines 5 followed by acylation with 12 acid chlorides to provide, upon cleavage from the resin, 60 individual N-substituted-N-acylglycines 7. The glycines 7 were converted to munchnones 8 by treatment with trifluoroacetic anhydride followed by reaction with benzamidine to give trisubstituted-5-TFMK-imidazoles 9. The structural content of the library was analyzed using PlateView of the LCMS results, and individual members were isolated by automated preparative LCMS.
authors.affiliation: Monsanto Company, AG Sector, 800 N. Lindbergh Boulevard, St. Louis, Missouri 63167, USA. c.hamper@monsanto.com
authors.forename: B C
authors.initials: BC
authors.lastname: Hamper
authors.forename: K D
authors.initials: KD
authors.lastname: Jerome
authors.forename: G
authors.initials: G
authors.lastname: Yalamanchili
authors.forename: D M
authors.initials: DM
authors.lastname: Walker
authors.forename: R C
authors.initials: RC
authors.lastname: Chott
authors.forename: D A
authors.initials: DA
authors.lastname: Mischke
mesh_terms: D019992:Databases as Topic; D005998:Glycine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D008958:Models, Molecular; D012116:Resins, Plant
chemical_list: D007093:Imidazoles; D007202:Indicators and Reagents; D007659:Ketones; D012116:Resins, Plant; D005998:Glycine