Benzyl 2-[({[2-(diisopropylamino)ethyl]amino}carbonyl)amino]ethylcarbamate → N-(2-aminoethyl)-N'-[2-(diisopropylamino)ethyl]urea

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[CH:1]([N:4]([CH:24]([CH3:26])[CH3:25])[CH2:5][CH2:6][NH:7][C:8]([NH:10][CH2:11][CH2:12][NH:13]C(=O)OCC1C=CC=CC=1)=[O:9])([CH3:3])[CH3:2]>C(O)C.[OH-].[Pd+2].[OH-]>[NH3:4].[NH2:13][CH2:12][CH2:11][NH:10][C:8]([NH:7][CH2:6][CH2:5][N:4]([CH:24]([CH3:26])[CH3:25])[CH:1]([CH3:2])[CH3:3])=[O:9]

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실험 절차

A solution of benzyl 2-[({[2-(diisopropylamino)ethyl]amino}carbonyl)amino]ethylcarbamate (Preparation 50) (6.25 g, 14.45 mmol) in ethanol (100 ml) was hydrogenated at room temperature over palladium (II) hydroxide (250 mg) for 4 hours at 414 KPa. The catalyst was removed by filtration through Arbocel (trade mark) and solvent evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol:concentrated aqueous ammonia (90:10:1, by volume) changing to dichloromethane:methanol:concentrated aqueous ammonia (90:10:2, by volume) to afford the title compound as a yellow oil (3.6 g).