Ethanol → HCID 69083158, compound

HRID 1023457Notes

Reaction equation

HRID 1023457 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[CH:11][N:10]([CH3:13])[C:9]=2[C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH2:20])[CH:15]=2)=[CH:4][CH:3]=1.[C:21]([N:29]=C=O)(=[O:28])C1C=CC=CC=1.C(O)C.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[CH:11][N:10]([CH3:13])[C:9]=2[C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH:20][C:21]([NH2:29])=[O:28])[CH:15]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 78210Benzoyl isocyanateHCID 69083700HCID 69083700, compound

Product 1

HCID 69083158HCID 69083158, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

4-[5-(4-Fluoro-phenyl)-3-methyl-3H-imidazol-4-yl]-pyridin-2-ylamine (13 mg, 0.048 mmol) and benzoyl isocynate (8.6 mg, 0.058 mmol) are mixed in DCM (0.5 mL). The reaction is sealed and heated at 50° C. for 16 hrs. Then the solvent is removed and to the residue are added ethanol (0.5 mL) and potassium carbonate (10 mg, 0.073 mmol). The mixture is then heated at 80° C. for 45 min. The solvent is removed and the residue is partitioned between water (35 mL) and EtOAc (55 mL). The aqueous layer is separated and extracted with EtOAc (2×30 mL). The organic layers are combined and concentrated to give the crude product. The crude is recrystallized in DCM to give 15 mg of the titled product.

Workup

  1. customThe reaction is sealed
  2. customThen the solvent is removed and to the residue
  3. temperatureThe mixture is then heated at 80° C. for 45 min
  4. customThe solvent is removed
  5. customthe residue is partitioned between water (35 mL) and EtOAc (55 mL)
  6. customThe aqueous layer is separated
  7. extractionextracted with EtOAc (2×30 mL)
  8. concentrationconcentrated
  9. customto give the crude product
  10. customThe crude is recrystallized in DCM

Sources & evidence

ORD record
ord-930fd88d793f4907b63ebd0cd24fbd0e
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

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