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

HRID 1162316Notes

Reaction equation

HRID 1162316 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

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 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%).

Workup

  1. additionmixed for 15 minutes
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue and DBU (0.69 g) were dissolved in acetonitrile (15 ml)
  4. additiona solution of 4-chlorophenyl isocyanate (0.25 g) in acetonitrile (15 ml) was added dropwise
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe residue was purified with silica gel column (ethyl acetate to ethyl acetate/methanol=5/1)
  7. customThe product was recrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-39355ae19d1f47f082f2d5bd66472ec4
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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