Ethanol → HCID 69085448, compound

HRID 1023464Notes

Reaction equation

HRID 1023464 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][O:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH2:19])[CH:14]=2)=[CH:4][CH:3]=1.[C:20]([N:28]=C=O)(=[O:27])C1C=CC=CC=1.C(O)C.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.CCOC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[CH:10][O:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]([NH2:28])=[O:27])[CH:14]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 78210Benzoyl isocyanateHCID 69083608HCID 69083608, compound

Product 1

HCID 69085448HCID 69085448, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

4-[4-(4-Fluoro-phenyl)-oxazol-5-yl]-pyridin-2-ylamine (57 mg, 0.22 mmol) and benzoyl isocynate (39 mg, 0.27 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 (46 mg, 0.34 mmol). The mixture is then heated at 80° C. for 55 min. The solvent is removed and the residue is partitioned between water (25 mL) and EtOAc (35 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. EtOAc (2 mL) is added into the crude and a solid is formed. The solid is filtered, rinsed with more EtOAc and dried to give 40 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 55 min
  4. customThe solvent is removed
  5. customthe residue is partitioned between water (25 mL) and EtOAc (35 mL)
  6. customThe aqueous layer is separated
  7. extractionextracted with EtOAc (2×30 mL)
  8. concentrationconcentrated
  9. customto give the crude product
  10. customa solid is formed
  11. filtrationThe solid is filtered
  12. washrinsed with more EtOAc
  13. customdried

Sources & evidence

ORD record
ord-1899d90998324b9e910f816323a409fa
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

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