4-Toluenesulfonyl chloride → HCID 68820282, compound

HRID 9421Notes

Reaction equation

HRID 9421 reaction equation
ClC1C=C(C=CC=1)C(OO)=O.[CH3:12][C:13]([CH3:39])([S:35]([NH2:38])(=[O:37])=[O:36])[CH2:14][CH2:15][CH2:16][N:17]1[C:29]2[C:28]3[CH:27]=[CH:26][C:25]([Br:30])=[CH:24][C:23]=3[N:22]=[CH:21][C:20]=2[N:19]=[C:18]1[CH2:31][O:32][CH2:33][CH3:34].[OH-].[NH4+:41].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)(Cl)Cl.ClCCl>[CH3:39][C:13]([CH3:12])([S:35]([NH2:38])(=[O:36])=[O:37])[CH2:14][CH2:15][CH2:16][N:17]1[C:29]2[C:28]3[CH:27]=[CH:26][C:25]([Br:30])=[CH:24][C:23]=3[N:22]=[C:21]([NH2:41])[C:20]=2[N:19]=[C:18]1[CH2:31][O:32][CH2:33][CH3:34]

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 68818014dimethyl 4-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butane-1-sulfonamide

Product 1

HCID 68820282HCID 68820282, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

3-Chloroperoxybenzoic acid (0.126 g of 70% pure material, 0.73 mmol) was added in one portion to a stirred solution of dimethyl 4-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butane-1-sulfonamide (0.30 g, 0.63 mmol) in chloroform (7 mL), and the solution was stirred for two hours at ambient temperature. Ammonium hydroxide (2 mL) and p-toluenesulfonyl chloride (0.15 g, 0.76 mmol) were sequentially added, and the mixture was stirred at ambient temperature for one hour. Dichloromethane (100 mL) was added, and the mixture was washed sequentially with 2 M aqueous sodium hydroxide (2×30 mL), saturated aqueous sodium bicarbonate (2×30 mL), and brine (30 mL); dried over magnesium sulfate; filtered; and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting with ethyl acetate:ethanol in a gradient from 100:0 to 80:20) followed by recrystallization from dichloromethane:heptane. The crystals were dried for two hours under vacuum at 40° C. to provide 0.185 g of dimethyl 4-(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butane-1-sulfonamide as a white solid, mp 193° C.

Workup

  1. stirringthe mixture was stirred at ambient temperature for one hour
  2. washthe mixture was washed sequentially with 2 M aqueous sodium hydroxide (2×30 mL), saturated aqueous sodium bicarbonate (2×30 mL), and brine (30 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationand concentrated under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel (
  7. washeluting with ethyl acetate
  8. customethanol in a gradient from 100:0 to 80:20) followed by recrystallization from dichloromethane
  9. customThe crystals were dried for two hours under vacuum at 40° C.

Sources & evidence

ORD record
ord-83171146c9b84b97aff0b1aa7d924e60
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

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