4-Toluenesulfonyl chloride → 1-[3-(aminooxy)propyl]-7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine

HRID 1992607Notes

Reaction equation

HRID 1992607 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]([CH2:15][CH2:16][CH2:17][O:18][N:19]4C(=O)C5C(=CC=CC=5)C4=O)[C:13]([CH2:30][CH2:31][CH3:32])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1.C1C=C(Cl)C=C(C(OO)=O)C=1.[OH-].[NH4+:45].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[NH2:19][O:18][CH2:17][CH2:16][CH2:15][N:14]1[C:6]2[C:5]3[CH:4]=[CH:3][C:2]([Br:1])=[CH:11][C:10]=3[N:9]=[C:8]([NH2:45])[C:7]=2[N:12]=[C:13]1[CH2:30][CH2:31][CH3:32]

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 685384882-[3-(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)propoxy]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 685393861-[3-(aminooxy)propyl]-7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-[3-(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)propoxy]-1H-isoindole-1,3(2H)-dione (1.00 g, 2.03 mmol) in chloroform (20 mL) at room temperature and under an atmosphere of nitrogen was added mCPBA (1.00 g, 4.06 mmol). The reaction was stirred for 2 hours, then was cooled to 0° C. Concentrated ammonium hydroxide (1 mL) was added followed by p-toluenesulfonyl chloride (111 mg, 0.58 mmol) in portions. The mixture was stirred for 1.5 hours at 0° C. and then filtered to remove a solid, which was washed with chloroform. The filtrate was washed with brine (2×10 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 0-35% CMA in chloroform) to afford 300 mg of 1-[3-(aminooxy)propyl]-7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine.

Workup

  1. stirringThe mixture was stirred for 1.5 hours at 0° C.
  2. filtrationfiltered
  3. customto remove a solid, which
  4. washwas washed with chloroform
  5. washThe filtrate was washed with brine (2×10 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 0-35% CMA in chloroform)

Sources & evidence

ORD record
ord-c990d3aec3e2415985945fb98817c458
Source dataset
uspto-grants-2010_01
Patent number
US07648997B2

Reaction notes

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