Facile synthesis of substituted 5-amino- and 3-amino-1,2,4-thiadiazoles from a common precursor.
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.
Wehn
Paul M
PM
Department of Medicinal Chemistry, Amgen Inc., 1120 Veterans Boulevard, South San Francisco, California 94080, USA. pwehn@amgen.com
Harrington
Paul E
PE
Eksterowicz
John E
JE
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
D006842:Hydrocarbons, Brominated; D013830:Thiadiazoles; D010165:Palladium