Patent ID: 6420556
Filing Date: 2002-07-16
Classification: C07C

Abstract:
A process for making guanidine compounds: and related cyclized compounds: using a solid-support resin, comprising the following steps:(b) reacting an acyl isothiocyanate resin â€ƒwherein â€”Lâ€” is a linking moiety, and â€”X is nil or one or two non-hydrogen substituents independently selected from alkyl, alkoxy, alkylthio, halo, and nitro, with a primary amine: R1â€”NH2, wherein R1 is selected from â€”R, â€”C(O)R, â€”CO2R, â€”C(O)NHR, â€”C(O)NR2, â€”NHR, â€”NR2, wherein R is selected from alkyl, aryl, and heterocycle, to provide: (c) reacting the product from Step (b) with a sulfur activating agent and ammonia or a primary or secondary amine: â€ƒwherein R2 and R3 are each independently selected from hydrogen, alkyl, aryl, and heterocycle, to provide: or, if R3 contains a displaceable group: â€ƒwherein is derved from R3, A being selected from alkylene, arylene, and alkarylene, and B being nil or one or more non-hydrogen substituents selected from â€”R, â€”OH, â€”OR, â€”SH, â€”SR, â€”NH2, â€”NHR, â€”NR2, &boxH;O, and &boxH;S, wherein R is selected from alkyl, aryl and heterocycle; (d) treating the product from Step (c) with a strong base or medium strength acid to cleave product from the resin, providing the guanidine compound or/and the related cyclized compound.