4-Toluenesulfonyl chloride → 1H-Imidazo[4,5-c]quinolin-4-amine, 1-[3-(aminooxy)propyl]-2-propyl-

HRID 1992579Notes

Reaction equation

HRID 1992579 reaction equation
[OH-].[NH4+:2].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[O-][N+:15]1[C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:18]2[N:25]([CH2:31][CH2:32][CH2:33][O:34][N:35]3C(=O)C4C(=CC=CC=4)C3=O)[C:26]([CH2:28][CH2:29][CH3:30])=[N:27][C:17]=2[CH:16]=1>C(Cl)(Cl)Cl>[NH2:35][O:34][CH2:33][CH2:32][CH2:31][N:25]1[C:18]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[N:15]=[C:16]([NH2:2])[C:17]=2[N:27]=[C:26]1[CH2:28][CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 68534464HCID 68534464, compound

Product 1

HCID 114494201H-Imidazo[4,5-c]quinolin-4-amine, 1-[3-(aminooxy)propyl]-2-propyl-

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Ammonium hydroxide (75 mL) and p-toluenesulfonyl chloride (4.87 g, 25.6 mmol) were added to a solution of 2-[3-(5-oxido-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)propoxy]-1H-isoindole-1,3(2H)-dione (10.0 g, 23.2 mmol) in chloroform (100 mL), and the resulting mixture was stirred vigorously for one hour.) A white precipitate was removed by filtration, and the filtrate layers were separated. The organic solution was washed with brine (2×150 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide a yellow solid. The solid was purified by column chromatography on silica gel (eluting with dichloromethane:methanol:ammonium hydroxide ranging in ratios from 94:5:1 to 91:8:1) to provide 4.31 g of 1-[3-(aminooxy)propyl]-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine as a beige powder, melting point (mp) 145-148° C.

Workup

  1. custom) A white precipitate was removed by filtration
  2. customthe filtrate layers were separated
  3. washThe organic solution was washed with brine (2×150 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto provide a yellow solid
  8. customThe solid was purified by column chromatography on silica gel (eluting with dichloromethane:methanol:ammonium hydroxide ranging in ratios from 94:5:1 to 91:8:1)

Sources & evidence

ORD record
ord-59b89e5244454c0fb4750ff60af4704c
Source dataset
uspto-grants-2010_01
Patent number
US07648997B2

Reaction notes

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