Hydrochloric Acid → N-(4-chlorophenyl)-N'-(1-((4-(5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperidinyl)carbonyl)pentyl)urea

Reaction equation

[CH3:1][C:2]1[N:6]2[C:7](=[O:31])[N:8]([CH:10]3[CH2:15][CH2:14][N:13]([C:16]([CH:18]([NH:23][C:24](=[O:30])OC(C)(C)C)[CH2:19][CH2:20][CH2:21][CH3:22])=[O:17])[CH2:12][CH2:11]3)[CH2:9][C:5]2=[CH:4][N:3]=1.[ClH:32].[CH2:33](O)[CH3:34]>>[Cl:32][C:34]1[CH:33]=[CH:15][C:10]([NH:8][C:24]([NH:23][CH:18]([C:16]([N:13]2[CH2:12][CH2:11][CH:10]([N:8]3[CH2:9][C:5]4=[CH:4][N:3]=[C:2]([CH3:1])[N:6]4[C:7]3=[O:31])[CH2:15][CH2:14]2)=[O:17])[CH2:19][CH2:20][CH2:21][CH3:22])=[O:30])=[CH:11][CH:12]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 702Ethanol

HCID 23138327tert-butyl 1-((4-(5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperidinyl)carbonyl)pentylcarbamate

Product 1

HCID 23138215N-(4-chlorophenyl)-N'-(1-((4-(5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperidinyl)carbonyl)pentyl)ureaYield 51%

Procedure

To tert-butyl 1-((4-(5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperidinyl)carbonyl)pentylcarbamate (0.65 g) obtained in Example 80b) was added concentrated hydrochloric acid (5 ml), and mixed for 15 minutes. To the reaction solution was added ethanol, and then concentrated under reduced pressure. The residue and DBU (0.69 g) were dissolved in acetonitrile (15 ml), and a solution of 4-chlorophenyl isocyanate (0.25 g) in acetonitrile (15 ml) was added dropwise thereto. After reacting for 15 hours, the solvent was distilled off under reduced pressure, and the residue was purified with silica gel column (ethyl acetate to ethyl acetate/methanol=5/1). The product was recrystallized from ethyl acetate-diisopropyl ether to obtain the title compound as colorless powder (0.37 g, 51%).