4-Toluenesulfonyl chloride → HCID 10423967, compound

HRID 1373940Notes

Reaction equation

HRID 1373940 reaction equation
[CH:1]([NH:4][N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:7]=[C:6]1[CH2:18][CH2:19][CH3:20])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=O)C=1.[OH-].[NH4+:33].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)(Cl)Cl.O>[CH:1]([NH:4][N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:33])[C:8]=2[N:7]=[C:6]1[CH2:18][CH2:19][CH3:20])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 21075809HCID 21075809, compound

Product 1

HCID 10423967HCID 10423967, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

A solution of N-isopropyl-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)amine (2.48 g, 9.24 mmol) in 75 mL of chloroform was cooled in a cold water bath. The solution was treated with MCPBA (3.32 g, 11.6 mmol) over 6 min. The reaction was allowed to come to ambient temperature. After 1.5 h, TLC showed complete conversion to the 5-N-oxide intermediate. The reaction mixture was again cooled in a cold water bath and then treated with concentrated ammonium hydroxide solution (30 mL, 30%) and stirred rapidly. The reaction mixture was treated with p-toluenesulfonyl chloride (1.85 g, 9.70 mmol) over 5 min. The reaction was allowed to come to ambient temperature. After 30 min, the reaction mixture was diluted with 50 mL of chloroform and 30 mL of water and the phases were separated. The organic portion was washed with 5% Na2CO3 solution (30 mL), water (30 mL) and brine (30 mL). The organic portion was dried over Na2SO4, filtered and concentrated under reduced pressure to yield a light brown foam. The material was purified by chromatography (SiO2, 97:3 CHCl3:MeOH) and recrystallized from EtOAc to yield 1.39 g of N1-isopropyl-2-propyl-1H-imidazo[4,5-c]quinoline-1,4-diamine as amber crystals.

Workup

  1. customto come to ambient temperature
  2. temperatureThe reaction mixture was again cooled in a cold water bath
  3. customto come to ambient temperature
  4. waitAfter 30 min
  5. customthe phases were separated
  6. washThe organic portion was washed with 5% Na2CO3 solution (30 mL), water (30 mL) and brine (30 mL)
  7. dry with materialThe organic portion was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto yield a light brown foam
  11. customThe material was purified by chromatography (SiO2, 97:3 CHCl3:MeOH)
  12. customrecrystallized from EtOAc

Sources & evidence

ORD record
ord-a956ce6dfb6f45d085cc005ce006cd99
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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