Pyridine → HCID 178490872, compound

HRID 388588Notes

Reaction equation

HRID 388588 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[Cl:13][C:14]1[C:23]([NH2:24])=[C:22]([NH:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1.N1C=CC=CC=1.C(#N)C>C1COCC1>[Cl:13][C:14]1[C:23]2[N:24]=[C:1]([OH:2])[N:25]([CH2:26][C:27]3[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=3)[C:22]=2[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:15]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6342AcetonitrileHCID 682631,1'-Carbonyldiimidazole3×HCID 86633716HCID 86633716, compound

Product 1

HCID 178490872HCID 178490872, compoundYield 41.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

1,1′-Carbonyldiimidazole (6.53 g, 40.3 mmol) was added to a solution of 2-chloro-N4-(4-methoxybenzyl)quinoline-3,4-diamine (11.49 g, 36.62 mmol) and pyridine (75 mL) in THF (75 mL), and the reaction was heated at 80° C. overnight. An analysis by LC/MS indicated the presence of starting material, and additional 1,1′-carbonyldiimidazole (1 equivalent) was added. The reaction was stirred overnight at 80° C., and additional 1,1′-carbonyldiimidazole (1 equivalent) was added. The reaction was stirred overnight at 80° C. and allowed to cool, and the solvent was removed under reduced pressure. The residue was dissolved in dichloromethane (500 mL), and the resulting solution was washed sequentially with brine and water, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide a solid. The solid was mixed with acetonitrile and isolated by filtration to provide 5.2 g of 4-chloro-1-(4-methoxybenzyl)-1H-imidazo[4,5-c]quinolin-2-ol.

Workup

  1. additionwas added
  2. stirringThe reaction was stirred overnight at 80° C.
  3. temperatureto cool
  4. customthe solvent was removed under reduced pressure
  5. dissolutionThe residue was dissolved in dichloromethane (500 mL)
  6. washthe resulting solution was washed sequentially with brine and water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto provide a solid
  11. customisolated by filtration

Sources & evidence

ORD record
ord-f57afb5205d64210b909d7b6c61d145b
Source dataset
uspto-grants-2013_02
Patent number
US08377957B2

Reaction notes

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