Ethanol → HCID 69092663, compound

HRID 1023462Notes

Reaction equation

HRID 1023462 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[CH:11]=[N:10][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]([CH3:13])[CH:11]=[N:10][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 69093926HCID 69093926, compound

Product 1

HCID 69092663HCID 69092663, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

4-[5-(4-Fluoro-phenyl)-1-methyl-1H-imidazol-4-yl]-pyridin-2-ylamine (72 mg, 0.27 mmol) and benzoyl isocynate (59 mg, 0.40 mmol) are mixed in DCM (2.0 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 (2.0 mL) and potassium carbonate (56 mg, 0.40 mmol). The mixture is then heated at 80° C. for 35 min. The solvent is removed and the residue is partitioned between water (35 mL) and EtOAc (45 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 washed with methanol (3×5 mL) and dried to give 55 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 35 min
  4. customThe solvent is removed
  5. customthe residue is partitioned between water (35 mL) and EtOAc (45 mL)
  6. customThe aqueous layer is separated
  7. extractionextracted with EtOAc (2×30 mL)
  8. concentrationconcentrated
  9. customto give the crude product
  10. washThe crude is washed with methanol (3×5 mL)
  11. customdried

Sources & evidence

ORD record
ord-57951b15a8bb4ed599ba9688a849b0bc
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

Loading…