4-Fluoroaniline → HCID 178512263, compound

HRID 1353394Notes

Reaction equation

HRID 1353394 reaction equation
C1C=CC(O[C:8](OC2C=CC=CC=2)=[N:9][C:10]#[N:11])=CC=1.[F:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1.[Cl:27][C:28]1[CH:37]=[C:36]2[C:31]([C:32]([N:38]3[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]3)=[CH:33][CH:34]=[N:35]2)=[CH:30][CH:29]=1>C(O)(C)C>[Cl:27][C:28]1[CH:37]=[C:36]2[C:31]([C:32]([N:38]3[CH2:43][CH2:42][N:41]([C:8](=[N:9][C:10]#[N:11])[NH:24][C:23]4[CH:25]=[CH:26][C:20]([F:19])=[CH:21][CH:22]=4)[CH2:40][CH2:39]3)=[CH:33][CH:34]=[N:35]2)=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 97314-FluoroanilineHCID 688090Diphenyl N-CyanocarbonimidateHCID 7383897-Chloro-4-(piperazin-1-yl)quinoline

Product 1

HCID 178512263HCID 178512263, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Diphenyl cyanocarbonimidate (0.24 g, 1.0 mmol) and 4-fluoroaniline (104 4μL, 1.1 mmol) are stirred in isopropanol (10 mL) for 15 h. The reaction mixture is concentrated, and the residue dissolved in EtOAc. Washing with sat NaHCO3, drying (MgSO4) and removing the solvent delivers 0.34 g of N-cyano-N′-(4-fluorophenyl)-O-phenylisourea as a colorless solid. It is dissolved in pyridine (15 mL) and 7-chloro-4-(piperazin-1-yl)quinoline (0.25 g, 1.0 mmol) is added. The reaction mixture is heated at reflux for 4 h and afterwards concentrated. Column chromatography of the residue with hexane-EtOAc gives the title product as a colorless solid.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. dissolutionthe residue dissolved in EtOAc
  3. washWashing
  4. dry with materialdrying (MgSO4)
  5. customremoving the solvent
  6. dissolutionIt is dissolved in pyridine (15 mL)
  7. temperatureThe reaction mixture is heated
  8. temperatureat reflux for 4 h
  9. concentrationafterwards concentrated

Sources & evidence

ORD record
ord-8e092285fcf54b6da8636faeaac5ee27
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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