Patent ID: 6441176
Filing Date: 2002-08-27
Classification: A61P,C07D

Abstract:
A process for making N-(5-cyclopropyl-1-quinolin-5-yl-1H-pyrazole-4-carbonyl)-guanidine comprising:a. combining quinolin-5-yl-hydrazine and methyl-3-cyclopropyl-2-dimethylenamino-3-oxopropanoate in a reaction-inert solvent in the presence of an amine base to form 5-cyclopropyl-1-quinolin-5-yl-1H-pyrazole-4-carboxylic acid methyl ester; b. hydrolyzing the 5-cyclopropyl-1-quinolin-5-yl-1H-pyrazole-4-carboxylic acid methyl ester to form 5-cyclopropyl-1-quinolin-5-yl-1H-pyrazole-4-carboxylic acid; c. combining the 5-cyclopropyl-1-quinolin-5-yl-1H-pyrazole-4-carboxylic acid and thionyl chloride in toluene to form 5-cyclopropyl-1-quinolin-5-yl-1H-pyrazole-4-carboxylic acid chloride; and d. combining guanidine hydrochloride and sodium hydroxide to a suspension of the 5-cyclopropyl-1-quinolin-5-yl-1H-pyrazole-4-carboxylic acid chloride in tetrahydrofuran at a temperature of about âˆ’10Â° C. to about 10Â° C. for about 1 hour to about 3 hours.