4-Toluenesulfonyl chloride → HCID 66813869, compound

HRID 1097603Notes

Reaction equation

HRID 1097603 reaction equation
ClC1C=C(C=CC=1)C(OO)=O.[CH2:12]([N:19]1[C:31]2[C:30]3[CH:29]=[CH:28][C:27]([Br:32])=[CH:26][C:25]=3[N:24]=[CH:23][C:22]=2[N:21]=[C:20]1[NH2:33])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[OH-].[NH4+:46]>>[CH2:12]([N:19]1[C:31]2[C:30]3[CH:29]=[CH:28][C:27]([Br:32])=[CH:26][C:25]=3[N:24]=[C:23]([NH2:46])[C:22]=2[N:21]=[C:20]1[NH2:33])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 66814743HCID 66814743, compound

Product 1

HCID 66813869HCID 66813869, compound

Procedure

3-Chloroperoxybenzoic acid (3.7 g of approximately 77% pure material) was added to a solution of 1-benzyl-7-bromo-1H-imidazo[4,5-c]quinolin-2-amine (2.91 g, 8.24 mmol), and the reaction was stirred for two hours at room temperature. Concentrated aqueous ammonium hydroxide (50 mL) and p-toluenesulfonyl chloride (3.1 g, 16 mmol) were added, and the mixture was stirred overnight at room temperature. The organic layer was separated and washed with water (3×200 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product (1.88 g) was purified by automated flash chromatography (silica cartridge, eluting with aqueous ammonium hydroxide:methanol:dichloromethane in a gradient from 0:0:100 to 0.55:10.45:89) to provide 123 g of 1-benzyl-7-bromo-1H-imidazo[4,5-c]quinolin-2,4-diamine as a reddish-brown solid.

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. customThe organic layer was separated
  3. washwashed with water (3×200 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product (1.88 g) was purified by automated flash chromatography (silica cartridge
  8. washeluting with aqueous ammonium hydroxide

Sources & evidence

ORD record
ord-4402e95acc624dc4b692af66a8632bd1
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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