Process for the synthesis of bis-aryl diamidoxime compounds
AssigneesThe University of North Carolina at Chapel Hill, Georgia State University Research Foundation, Inc.
InventorsDavid W. Boykin, Mariappan Anbazhagan, Richard R. Tidwell
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Abstract
Bis-aryl diamidoxime compounds, such as 2,5-bis [4-hydroxy and 4-O-alkylamidinophenyl] furans, can be prepared from 2,5-bis tri-alkylstannanes via a one step palladium-catalyzed cross reaction. Bis-aryl diamidoxime compounds, such as 2,5-bis [4-hydroxy and 4-O-alkylamidinophenyl]furans, are useful as therapeutic compounds. The disclosed process is scalable, simpler, more economic and more feasible than other presently known methods of preparing 2,5-bis [4-hydroxy and 4-O-alkylamidinophenyl]furans and other bis-aryl diamidoxime compounds.
Claims9
A method of preparing a bis-aryl diamidoxime compound of formula (I):
- wherein:
- R, R1, and R2 are the same or different and are selected from the group consisting of H, aryl, linear alkyl, cyclic alkyl, and branched alkyl;
- Q is selected from the group consisting of O, S, NH and CH2;
- and pharmaceutically acceptable salts thereof;
- the method comprising:
- (a) contacting an amidoxime aryl halide with a 2,5-bis trialkylstannane compound under an anhydrous gas to form a first reaction mixture, wherein the amidoxime aryl halide has the following structure:
- wherein R, R1, and R2 are the same or different and are selected from the group consisting of H, aryl, linear alkyl, cyclic alkyl, and branched alkyl;
- and X is halogen;
- and
- wherein the 2,5-bis trialkylstannane has the following structure:
- wherein R3 is lower alkyl and Q is selected from the group consisting of O, S, NH and CH2;
- (b) adding an anhydrous aprotic solvent and a palladium catalyst to the first reaction mixture to form a second reaction mixture;
- and
- (c) refluxing the second reaction mixture for a period of time, whereby a bis-aryl diamidoxime compound of formula (I) is prepared.
Dependencies are inferred from the claim text.