Patent ID: 6933391

Claim:
A method of synthesizing a compound of Formula I having the structure: where all R and R* groups are independently: (i) R 2 ; (ii) halogen; (iii) —OR 2 ; (iv) —C(O)—OR 2 ; (v) —C(O)—N(R 2 ) 2 ; (vi) —N(R 2 ) 2 ; (vii) -alkyl-C(O)—OR 2 ; (viii) -alkyl-C(O)—N(R 2 ) 2 ; (ix) -alkyl-N(R 2 ) 2 ; (x) -aryl-C(O)—OR 2 ; (xi) -aryl-C(O)—N(R 2 ) 2 ; (xii) -aryl-N(R 2 ) 2 ; (xiii) acyl; (xiv) acyloxy; (xv) heterocyclo; (xvi) hydroxyalkyl; (xvii) —SO 2 —R 2 ; (xviii) -alkyl-SO 2 —R 2 ; (xix) -(A) p -R 3 , where A is a linking group, p is 0 or a positive integer, and R 3 is a bioactive moiety; or (xx) two R groups, or an R group and an R* group, taken together with the one or more atoms to which they are bonded, form a saturated or unsaturated, spiro or fused, carbocyclic (such as fused 1,2-phenyl) or heterocyclic ring which may be unsubstituted or substituted by one or more groups selected from the groups (i) to (xix) above; with the proviso that a carbon atom bearing an R group is not directly bonded to more than one heteroatom; and R 2 is independently hydrogen, alkyl, alkenyl, alkynyl, or aryl, the method comprising the steps of: (i) contacting 2-{2-(1,3-dioxoisoindolin-2-yl)-1-[(2-nitroimidazolyl)methyl]ethoxy}isoindoline- 1,3-dione: with hydrazine, to obtain 1-(3-amino-2-(aminooxy)propyl)-2-nitro-1H-imidazole dihydrochioride; and (ii) contacting the product of (i) with a compound having the structure IIIa or IIIb or a mixture thereof: where X is halogen and R and R* are defined above.