Patent ID: 7037933

Claim:
A method of synthesizing a compound of Formula I or Formula II: wherein Z 1 and Z 2 may be the same, or different, and are a halogen selected from the group consisting of iodine, fluorine, bromine, and chlorine; X can be O, S, or NH; m is from 0 to 4; p is 0 or 1; R is H, OH, NH 2 , SH, halide, alkyl, O-alkyl, acyl, O-acyl, aryl, O-aryl, substituted amine, or substituted thiol; R 1 and R 2 can be the same or different and are, independently H, methyl, ethyl, propyl, with the proviso that R 1 and R 2 are not both H; alternatively, R 1 and R 2 , together, can form a cyclopropyl, cyclobutyl, cyclopentyl, or a cyclohexyl group; Y is OR 5 , wherein R 5 is a straight or branched chain alkyl or heteroalkyl having 1 to 8 carbon atoms, a substituted or unsubstituted aryl or heteroaryl; or wherein R 6 and R 7 are independently selected from H, alkyl or heteroalkyl of 1 to 6 carbon atoms, or wherein N is part of a cyclic or heterocyclic group comprising morpholine, triazole, imidazole, pyrrolidine, piperidine, piperazine, pyrrole, dihydropyridine, aziridine, thiazolidine, thiazoline, thiadiazolidine, or thiadiazoline; and R 3 and R 4 can be the same or different and can be a moiety selected from the group consisting of C n-20 alkyl, C 1-20 heteroalkyl, C 2-20 alkenyl, aryl, C 1-20 alkyl-aryl, C 2-20 alkenyl-aryl, heteroaryl, C 1-20 alkyl-heteroaryl, C 2-20 alkenyl-heteroaryl, cycloalkyl, heterocycloalkyl, C 1-20 alkyl-heterocycloalkyl, and C 1-20 alkyl-cycloalkyl, any of which may be, optionally, substituted with a moiety selected from the group consisting of C 1-6 alkyl, halogen, CN, NO 2 , or SO 2-4 , or wherein N is part of a cyclic or heterocyclic group, preferentially, but not limited to, morpholine, triazole, imidazole, pyrrolidine, piperidine, piperazine, pyrrole, dihydropyridine, aziridine, thiazolidine, thiazoline, thiadiazolidine, or thiadiazoline; wherein n is from 1–19; comprising: a) treating a compound of the Formula A: wherein Xa is —OH, —NH 2 or —SH and Z- represents Cl—, Br—or I—, with a compound of the Formula B: Cl(O)C(CH 2 ) m (CR 1 R 2 ) p W Formula B wherein W is Y or —(O)CH(CH 3 )(CHR 3 R 4 ), wherein Y, R 3 and R 4 are as defined above, to produce a compound of the Formula C: wherein X, W, R 1 , R 2 , m and p are as defined above; b) treating a compound of Formula C with a compound of Formula D: wherein Z 1 and Z 2 are as defined above and R′ is a protecting group, to form a compound of the Formula E: wherein X, W, R 1 , R 2 , Z 1 , Z 2 , m and p are as defined above; c) deprotecting the compound of Formula E to form a compound of Formula F: d) treating the compound of Formula F with diethylaminoethyl-L, wherein L is a leaving group, in the presence of a base to form a compound of Formula I or Formula II.