4-Toluenesulfonyl chloride → 7-(furan-3-ylmethoxy)-2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine

HRID 598347Notes

Reaction equation

HRID 598347 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH2:6][O:7][C:8]2[CH:9]=[CH:10][C:11]3[C:12]4[N:20]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:19]([CH3:25])=[N:18][C:13]=4[CH:14]=[N:15][C:16]=3[CH:17]=2)=[CH:2]1.ClC1C=C(C=CC=1)C(OO)=O.[OH-].[NH4+:38].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>ClCCl>[O:1]1[CH:5]=[CH:4][C:3]([CH2:6][O:7][C:8]2[CH:9]=[CH:10][C:11]3[C:12]4[N:20]([CH2:21][CH:22]([CH3:23])[CH3:24])[C:19]([CH3:25])=[N:18][C:13]=4[C:14]([NH2:38])=[N:15][C:16]=3[CH:17]=2)=[CH:2]1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 670510517-(furan-3-ylmethoxy)-2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

Product 1

HCID 575453267-(furan-3-ylmethoxy)-2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-(Furan-3-ylmethoxy)-2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline (500 mg) was dissolved in 30 mL of dichloromethane and 3-chloroperoxybenzoic acid (60% pure, 403 mg) was added. The reaction was stirred for 30 minutes at ambient temperature and then 30 mL of aqueous ammonium hydroxide was added. After 10 minutes, p-toluenesulfonyl chloride (268 mg, 1.40 mmol) was added and the reaction was stirred for an additional 15 minutes. The layers were separated and the aqueous fraction was washed with two portions of dichloromethane (20 mL). The organic fractions were combined and washed three times with 20 mL portions of aqueous sodium carbonate. The combined sodium carbonate fractions were extracted with four portions of chloroform (20 mL). All of the organic fractions were combined, dried over magnesium sulfate, and concentrated to yield an orange foam. The crude product was purified using flash column chromatography on silica gel, eluting with a gradient of methanol in chloroform. The clean fractions were combined, concentrated, and the resulting solid was recrystallized from acetonitrile to give 102 mg of 7-(furan-3-ylmethoxy)-2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine as a white powder, mp 181.0-183.0.

Workup

  1. waitAfter 10 minutes
  2. stirringthe reaction was stirred for an additional 15 minutes
  3. customThe layers were separated
  4. washthe aqueous fraction was washed with two portions of dichloromethane (20 mL)
  5. washwashed three times with 20 mL portions of aqueous sodium carbonate
  6. extractionThe combined sodium carbonate fractions were extracted with four portions of chloroform (20 mL)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customto yield an orange foam
  10. customThe crude product was purified
  11. washeluting with a gradient of methanol in chloroform
  12. concentrationconcentrated
  13. customthe resulting solid was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-c5fcc563ad1744979bad8a983fc8cd22
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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