Ethanol → HCID 69084231, compound

HRID 1023420Notes

Reaction equation

HRID 1023420 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH2:19])[CH:14]=3)=[CH:11][CH:10]=[N:9]2)=[CH:4][CH:3]=1.[C:20]([N:28]=C=O)(=[O:27])C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].C(O)C>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]([NH2:28])=[O:27])[CH:14]=3)=[CH:11][CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 78210Benzoyl isocyanateHCID 69086111HCID 69086111, compound

Product 1

HCID 69084231HCID 69084231, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To the solution of 4-[2-(4-Fluoro-phenyl)-2H-pyrazol-3-yl]-pyridin-2-ylamine (83 mg, 0.33 mmol) in DCM (3.0 mL) is added benzoyl isocynate (96 mg, 0.65 mmol). The resulting mixture is heated at 50° C. for 1 hour. The solvent is then carefully removed in vacuum and to the residue are added K2CO3 (54 mg, 0.39 mmol) and ethanol (2 mL). The reaction mixture is then heated at 85° C. for 30 min. Solvent is again removed in vacuum and the residue is purified through a Silica column eluting with 0-100% EtOAc/Heptane to give the titled compound (72 mg).

Workup

  1. customThe solvent is then carefully removed in vacuum and to the residue
  2. temperatureThe reaction mixture is then heated at 85° C. for 30 min
  3. customSolvent is again removed in vacuum
  4. customthe residue is purified through a Silica column
  5. washeluting with 0-100% EtOAc/Heptane

Sources & evidence

ORD record
ord-44ee4a0dd2f64dcfa5f58724908872d8
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

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