4-Toluenesulfonyl chloride → HCID 57447010, compound

HRID 2366590Notes

Reaction equation

HRID 2366590 reaction equation
C1C=C(Cl)C=C(C(OO)=O)C=1.[CH3:12][NH:13][C:14](=[O:34])[CH2:15][CH2:16][CH2:17][N:18]1[C:30]2[C:29]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[N:23]=[CH:22][C:21]=2[N:20]=[C:19]1[CH2:31][CH2:32][CH3:33].[OH-].[NH4+:36].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[NH2:36][C:22]1[C:21]2[N:20]=[C:19]([CH2:31][CH2:32][CH3:33])[N:18]([CH2:17][CH2:16][CH2:15][C:14]([NH:13][CH3:12])=[O:34])[C:30]=2[C:29]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[N:23]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 68932042HCID 68932042, compound

Product 1

HCID 57447010HCID 57447010, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

mCPBA (3.3 g, 15 mmol) was added to a solution of N-methyl-4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butanamide (1.83 g, 5.90 mmol) in chloroform (75 mL), and the reaction was stirred for 1.5 hours at ambient temperature. Concentrated ammonium hydroxide (75 mL of 29%) and p-toluenesulfonyl chloride (1.7 g, 8.9 mmol) were then sequentially added with stirring, and the reaction was stirred for 45 minutes. The aqueous layer was separated and extracted with chloroform (1×50 mL). The combined organic fractions were washed with 5% aqueous sodium hydroxide solution (2×50 mL), dried over potassium carbonate, filtered, and concentrated under reduced pressure. The residue was recrystallized from a mixture of toluene (20 mL) and methanol (4 mL) and then recrystallized three times from 5:1 methanol:water (18 mL) and dried overnight in a vacuum oven at 80° C. During the recrystallization, the product was mixed with material from another run to provide 0.720 g of 4-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-N-methylbutanamide as a tan solid, hp 177-179° C.

Workup

  1. stirringwith stirring
  2. stirringthe reaction was stirred for 45 minutes
  3. customThe aqueous layer was separated
  4. extractionextracted with chloroform (1×50 mL)
  5. washThe combined organic fractions were washed with 5% aqueous sodium hydroxide solution (2×50 mL)
  6. dry with materialdried over potassium carbonate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was recrystallized from a mixture of toluene (20 mL) and methanol (4 mL)
  10. customrecrystallized three times from 5:1 methanol
  11. dry with materialwater (18 mL) and dried overnight in a vacuum oven at 80° C
  12. customDuring the recrystallization
  13. additionthe product was mixed with material from another run

Sources & evidence

ORD record
ord-14556aa08eae4e9ba8832f64ab65c9f7
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

Loading…