4-Chlorophenyl Isocyanate → N-(4-chlorophenyl)-N'-(2-(4-(5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperidinyl)-2-oxo-1-phenylethyl)urea

HRID 1162305Notes

Reaction equation

HRID 1162305 reaction equation
[NH2:1][CH:2]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([N:11]2[CH2:15][C:14]3=[CH:16][N:17]=[C:18]([CH3:19])[N:13]3[C:12]2=[O:20])[CH2:7][CH2:6]1)=[O:4].[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]=[C:35]=[O:36])=[CH:30][CH:29]=1>CN(C=O)C.C(OCC)(=O)C>[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:35]([NH:1][CH:2]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:3]([N:5]2[CH2:10][CH2:9][CH:8]([N:11]3[CH2:15][C:14]4=[CH:16][N:17]=[C:18]([CH3:19])[N:13]4[C:12]3=[O:20])[CH2:7][CH2:6]2)=[O:4])=[O:36])=[CH:30][CH:29]=1

Participants

5

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 231380962-(1-(2-amino-2-phenylacetyl)-4-piperidinyl)-5-methyl-1,2-dihydro-3H-imidazo[1,5-c]imidazol-3-one

Product 1

HCID 23138178N-(4-chlorophenyl)-N'-(2-(4-(5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperidinyl)-2-oxo-1-phenylethyl)ureaYield 62.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(1-(2-Amino-2-phenylacetyl)-4-piperidinyl)-5-methyl-1,2-dihydro-3H-imidazo[1,5-c]imidazol-3-one (0.10 g) obtained in Example 50b) was dissolved in DMF (3.0 ml), 4-chlorophenyl isocyanate (0.05 g) was added thereto, and mixed at room temperature for 1 hour. The reaction mixture was dissolved in ethyl acetate, washed with an aqueous sodium hydrogen carbonate solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified with basic silica gel column (ethyl acetate to methanol/ethyl acetate=1/10). The product was crystallized from ethyl acetate-diethyl ether to obtain the title compound as colorless powder (0.09 g, 59%).

Workup

  1. additionmixed at room temperature for 1 hour
  2. washwashed with an aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified with basic silica gel column (ethyl acetate to methanol/ethyl acetate=1/10)
  6. customThe product was crystallized from ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-5ee362b88ee94a169682e8432becb5bc
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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