4-Toluenesulfonyl chloride → HCID 57447011, compound

HRID 2366593Notes

Reaction equation

HRID 2366593 reaction equation
[CH2:1]([C:4]1[N:5]([CH2:17][CH2:18][CH2:19][C:20]([NH2:22])=[O:21])[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:16]=1)[CH2:2][CH3:3].C1C=C(Cl)C=C(C(OO)=O)C=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[OH-].[NH4+:46]>>[NH2:46][C:8]1[C:7]2[N:16]=[C:4]([CH2:1][CH2:2][CH3:3])[N:5]([CH2:17][CH2:18][CH2:19][C:20]([NH2:22])=[O:21])[C:6]=2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:9]=1

Participants

5

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 57447012HCID 57447012, compound

Product 1

HCID 57447011HCID 57447011, compound

Procedure

4-(2-Propyl-1H-imidazo[4,5-c]quinolin-1-yl)butanamide (2.90 g, 9.78 mmol) was treated with mCPBA (5.5 g, 25 mmol), concentrated ammonium hydroxide (100 mL of 29%), and p-toluenesulfonyl chloride (2.80 g, 14.7 mmol) according to the method described in Part E of Example 3. After the reaction solution was dried with potassium carbonate, it was decanted, and charcoal (2 g) was added. The mixture was heated at reflux for two hours, filtered through a layer of CELITE filter agent, and concentrated under reduced pressure. The crude solid was purified by column chromatography on silica gel (eluting with 90:10 dichloromethane:methanol) and combined with material from another run. The solid was recrystallized from 5:1 toluene:methanol (18 mL), dried overnight in a vacuum oven, recrystallized from ethanol:water, and dried overnight in a vacuum oven to provide 4-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butanamide as a tan solid, mp 249-251° C.

Workup

  1. dry with materialAfter the reaction solution was dried with potassium carbonate, it
  2. customwas decanted
  3. additioncharcoal (2 g) was added
  4. temperatureThe mixture was heated
  5. temperatureat reflux for two hours
  6. filtrationfiltered through a layer of CELITE filter agent
  7. concentrationconcentrated under reduced pressure
  8. customThe crude solid was purified by column chromatography on silica gel (eluting with 90:10 dichloromethane:methanol)
  9. customThe solid was recrystallized from 5:1 toluene
  10. dry with materialmethanol (18 mL), dried overnight in a vacuum oven
  11. customrecrystallized from ethanol
  12. dry with materialwater, and dried overnight in a vacuum oven

Sources & evidence

ORD record
ord-f060f241557d40179a296bea82693a31
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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