Patent ID: 6413785
Filing Date: 2002-07-02
Classification: C07D,C40B

Abstract:
A process for making 1-aminohydantoin compounds: using a solid-support resin having a linking moiety capable of reacting with a carboxylic acid and attaching it to the resin, comprising the following steps:(a) preparing a resin-bound, N-protected &agr;-hydrazinyl ester: â€ƒwhere Bl is a N-protecting group; (1) by reacting the resin with an &agr;-bromo carboxylic acid, then with a N-protected hydrazine; or (2) by reacting the resin with a N-protected &agr;-hydrazinyl carboxylic acid; (b) preparing a resin-bound imine: â€ƒby removing the N-protecting group from the hydrazinyl moiety of the resin-bound, N-protected &agr;-hydrazinyl ester; then reacting the unprotected hydrazinyl moiety with an aldehyde or a ketone; (c) preparing a resin-bound secondary urea: (1) by reacting the resin-bound imine with p-nitrophenylchloroformate or triphosgene, then with a primary amine; or (2) by reacting the resin-bound imine with an isocyanate; (d) preparing the 1-aminohydantoin compound by removing the resin-bound secondary urea from the resin and cyclizing it; R1, R2, R3, R4 and R5 each independently being any moiety that is stable throughout the process.