1-[3-(benzyloxycarbonylamino)propyl]-4-chloro-1H-imidazo[4,5-c]quinoline → 1-(3-aminopropyl)-4-chloro-1H-imidazo[4,5-c]quinoline.acetate

HRID 1108627Notes

Reaction equation

HRID 1108627 reaction equation
Br.[C:2]([OH:5])(=[O:4])[CH3:3].C(OC([NH: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]=[C:24]([Cl:33])[C:23]=2[N:22]=[CH:21]1)=O)C1C=CC=CC=1>>[NH2:16][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]=[C:24]([Cl:33])[C:23]=2[N:22]=[CH:21]1.[C:2]([O-:5])(=[O:4])[CH3:3]

Participants

3

Reactant 2

HCID 187839491-[3-(benzyloxycarbonylamino)propyl]-4-chloro-1H-imidazo[4,5-c]quinolineHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 867554221-(3-aminopropyl)-4-chloro-1H-imidazo[4,5-c]quinoline.acetate

Procedure

3 ml of 33% hydrogen bromide-acetic acid was added to 0.12 g (0.304 mmol) of 1-[3-(benzyloxycarbonylamino)propyl]-4-chloro-1H-imidazo[4,5-c]quinoline and the mixture was stirred at room tempterature for 1.5 hours. After the reaction mixture was concentrated under reduced pressure, a 1N sodium hydroxide aqueous solution and brine were added to the residue and the solution was extracted five times with chloroform. The organic phase was dried (Na2SO4), the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform:methanol:32% acetic acid=12:6:1 (v/v)) to obtain 60 mg (0.187 mmol) of 1-(3-aminopropyl)-4-chloro-1H-imidazo[4,5-c]quinoline·acetate shown below as a pale yellow solid. ##STR32## Its spectroscopic data are as follows: 1H-NMR (CD3OD) δ (ppm): 1.94 (3H, s), 2.39 (2H, m), 3.12 (2H, t, J=7.8 Hz), 4.82 (2H, t, J=7.2 Hz), 7.70 (2H, m), 7.97 (1H, d, J=8.0 Hz), 8.27 (1H, d, J=8.0 Hz), 8.41 (1H, s).

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure
  2. additiona 1N sodium hydroxide aqueous solution and brine were added to the residue
  3. extractionthe solution was extracted five times with chloroform
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (chloroform:methanol:32% acetic acid=12:6:1 (v/v))

Sources & evidence

ORD record
ord-ba1ddcee43b44f1ba42e164c36696b3c
Source dataset
uspto-grants-2000_05
Patent number
US06069149

Reaction notes

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