title: Facile synthesis of substituted 5-amino- and 3-amino-1,2,4-thiadiazoles from a common precursor.
abstract: A novel approach to the synthesis of substituted 5-amino- and 3-amino-1,2,4-thiadiazoles beginning from a common precursor has been achieved. Derivatization by palladium-catalyzed Suzuki-Miyaura coupling enables the rapid preparation of analogs around this pharmaceutically relevant core. FMO calculations rationalize the observed chemoselectivity for coupling at chlorine.
authors.affiliation: Department of Medicinal Chemistry, Amgen Inc., 1120 Veterans Boulevard, South San Francisco, California 94080, USA. pwehn@amgen.com
authors.forename: Paul M
authors.initials: PM
authors.lastname: Wehn
authors.forename: Paul E
authors.initials: PE
authors.lastname: Harrington
authors.forename: John E
authors.initials: JE
authors.lastname: Eksterowicz
mesh_terms: D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013830:Thiadiazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D006842:Hydrocarbons, Brominated; D013830:Thiadiazoles; D010165:Palladium