4-Toluenesulfonyl chloride → HCID 57447008, compound

HRID 2366587Notes

Reaction equation

HRID 2366587 reaction equation
[CH2:1]([NH:4][C:5](=[O:25])[CH2:6][CH2:7][CH2:8][N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[N:11]=[C:10]1[CH2:22][CH2:23][CH3:24])[CH2:2][CH3:3].C1C=C(Cl)C=C(C(OO)=O)C=1.[OH-].[NH4+:38].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C1(C)C=CC=CC=1.ClCCl>[NH2:38][C:13]1[C:12]2[N:11]=[C:10]([CH2:22][CH2:23][CH3:24])[N:9]([CH2:8][CH2:7][CH2:6][C:5]([NH:4][CH2:1][CH2:2][CH3:3])=[O:25])[C:21]=2[C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:14]=1

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 57447007HCID 57447007, compound

Product 1

HCID 57447008HCID 57447008, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

N-Propyl-4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butanamide (5.6 g, 15 mmol) was treated with mCPBA (8.5 g, 38 mmol), concentrated ammonium hydroxide (100 mL), and p-toluenesulfonyl chloride (4.9 g, 26 mmol) according to the method described in Part F of Example 1. The crude product was dissolved in hot toluene (25 mL) and dichloromethane. A precipitate slowly formed, was isolated by filtration, and was washed with toluene (15 mL). The solid was recrystallized twice from 4:1 methanol:water (25 mL), and the crystals were heated at reflux in chloroform in the presence of charcoal (1 g). The mixture was filtered through a layer of CELITE filter agent, and the filtrate was concentrated under reduced pressure. The residue was recrystallized twice from methanol:water and twice from toluene (15 mL) and dried overnight in a vacuum even to provide 0.74 g of 4-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-N-propylbutanamide as a grey solid, mp 161-163° C.

Workup

  1. customA precipitate slowly formed
  2. customwas isolated by filtration
  3. washwas washed with toluene (15 mL)
  4. customThe solid was recrystallized twice from 4:1 methanol
  5. temperaturewater (25 mL), and the crystals were heated
  6. temperatureat reflux in chloroform in the presence of charcoal (1 g)
  7. filtrationThe mixture was filtered through a layer of CELITE filter agent
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was recrystallized twice from methanol
  10. dry with materialwater and twice from toluene (15 mL) and dried overnight in a vacuum even

Sources & evidence

ORD record
ord-b1b2e47de1224538979f7145e2276c57
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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