4-Toluenesulfonyl chloride → HCID 57447022, compound

HRID 2366605Notes

Reaction equation

HRID 2366605 reaction equation
C1C=C(Cl)C=C(C(OO)=O)C=1.[CH3:12][NH:13][C:14](=[O:36])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]1[C:32]2[C:31]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[N:25]=[CH:24][C:23]=2[N:22]=[C:21]1[CH2:33][CH2:34][CH3:35].[OH-].[NH4+:38].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[NH2:38][C:24]1[C:23]2[N:22]=[C:21]([CH2:33][CH2:34][CH3:35])[N:20]([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:14]([NH:13][CH3:12])=[O:36])[C:32]=2[C:31]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[N:25]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 69506822HCID 69506822, compound

Product 1

HCID 57447022HCID 57447022, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

mCPBA (5.0 g, 29.03 mmol) was added to a solution of N-methyl-6-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)hexanamide (3.42 g, 9.67 mmol) in chloroform (100 mL). The reaction was stirred for two hours at ambient temperature and then washed with 10% aqueous sodium hydroxide. Ammonium hydroxide (40 mL) and p-toluenesulfonyl chloride (2.39 g, 12.6 mmol) were sequentially added, and the reaction was stirred vigorously for two hours. The organic layer was separated and washed sequentially with 10% sodium hydroxide, saturated aqueous sodium bicarbonate, and brine; dried over magnesium sulfate; filtered; and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting with 95:5 dichloromethane:methanol) followed by recrystallization from methanol:water to provide 1.055 g of 6-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-N-methylhexanamide as beige needles, mp 158-159° C.

Workup

  1. washwashed with 10% aqueous sodium hydroxide
  2. stirringthe reaction was stirred vigorously for two hours
  3. customThe organic layer was separated
  4. washwashed sequentially with 10% sodium hydroxide, saturated aqueous sodium bicarbonate, and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationand concentrated under reduced pressure
  8. customThe crude product was purified by column chromatography on silica gel (eluting with 95:5 dichloromethane:methanol)
  9. customfollowed by recrystallization from methanol

Sources & evidence

ORD record
ord-dabd37f67d584a71b75403c3db0c530f
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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