1-Pyrrolidinepropanamine → 1-(4-{[3-(4-Tert-butylphenyl)-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl]methyl}pyridin-2-yl)-3-(3-pyrrolidin-1-ylpropyl)urea

Participants

Reaction Conditions

Reaction Steps

To a solution of 100 mg of 3-(4-tert-butylphenyl)-5,5-dimethyl-1-[(2-thioxo-2H-[1,2,4]oxadiazolo[2,3-a]pyridin-7-yl)methyl]imidazolidine-2,4-dione obtained in stage b) below in 2 mL of dimethyl sulphoxide are added 120 mg of 3-pyrrolidin-1-ylpropan-1-amine. The solution is stirred at a temperature of 100° C. for 1 hour 40 minutes. After cooling to a temperature in the region of 20° C., the reaction medium is diluted with water, the suspension is filtered and the precipitate is purified by chromatography on a column of silica, eluting with a dichloromethane/methanol/28% aqueous ammonia mixture (gradient from 100/0 to 75/20/5 by volume). 18.5 mg of 1-(4-{[3-(4-tert-butylphenyl)-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl]methyl}pyridin-2-yl)-3-(3-pyrrolidin-1-ylpropyl)urea are obtained in the form of a pale yellow powder, the characteristics of which are as follows:

Provenance & Evidence