Methanol → HCID 23138126, compound

HRID 1162297Notes

Reaction equation

HRID 1162297 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][CH:12]([C:17]([N:19]2[CH2:24][CH2:23][N:22]([N:25]3[CH2:29][C:28]4=[CH:30][N:31]=[C:32]([CH3:33])[N:27]4[C:26]3=[O:34])[CH2:21][CH2:20]2)=[O:18])[C:13]([OH:16])([CH3:15])[CH3:14])=[O:10])=[CH:4][CH:3]=1.ClC(Cl)(Cl)[C:37]([N:39]=C=O)=[O:38].CO.C(=O)([O-])[O-].[K+].[K+]>ClCCl.O>[C:37](=[O:38])([O:16][C:13]([CH3:14])([CH3:15])[CH:12]([NH:11][C:9]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:10])[C:17]([N:19]1[CH2:24][CH2:23][N:22]([N:25]2[CH2:29][C:28]3=[CH:30][N:31]=[C:32]([CH3:33])[N:27]3[C:26]2=[O:34])[CH2:21][CH2:20]1)=[O:18])[NH2:39]

Participants

7

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 76400Trichloroacetyl isocyanateHCID 23138318HCID 23138318, compound

Product 1

HCID 23138126HCID 23138126, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N—(4-chlorophenyl)—N′—(2-hydroxy-2-methyl-1-((4-(5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperazinyl)carbonyl)propyl)urea (0.18 g) obtained in Example 34 in dichloromethane (15 ml) was added trichloroacetyl isocyanate (0.065 ml) at 0° C., and the temperature of the mixture was elevated to room temperature and mixed at room temperature for 6 hours. To the reaction mixture were added methanol (5 ml), water (5 ml) and potassium carbonate (0.15 g), and then mixed at room temperature for 15 hours. The reaction mixture was concentrated under reduced pressure, and then extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with basic silica gel column (ethyl acetate to ethyl acetate/methanol=10/1) to obtain the title compound as colorless powder (0.12 g, 62%).

Workup

  1. customwas elevated to room temperature
  2. additionmixed at room temperature for 6 hours
  3. additionmixed at room temperature for 15 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. extractionextracted with ethyl acetate
  6. dry with materialThe extract was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified with basic silica gel column (ethyl acetate to ethyl acetate/methanol=10/1)

Sources & evidence

ORD record
ord-807ae33da84c4754b6fd9387c2f94e15
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

Loading…