Toluene → 7-benzyloxy-2-ethoxymethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

HRID 2383089Notes

Reaction equation

HRID 2383089 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:20][CH2:21][CH:22]([CH3:24])[CH3:23])=[C:14]([NH2:19])[CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:25]([O:27][CH2:28][C:29](Cl)=O)[CH3:26].C1(C)C=CC=CC=1>N1C=CC=CC=1.C(N(CC)CC)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:20]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:26]([CH2:25][O:27][CH2:28][CH3:29])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 84189Ethoxyacetyl chlorideHCID 670509707-benzyloxy-N4-(2-methylpropyl)quinoline-3,4-diamine2×

Product 1

HCID 670509617-benzyloxy-2-ethoxymethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 8471TriethylamineSolvent

Procedure

The preparation of 7-benzyloxy-N4-(2-methylpropyl)quinoline-3,4-diamine is described in Parts A-F of Example 1. A concentrated solution of ethoxyacetyl chloride (12.2 g, 99.2 mmol) was added dropwise to a solution of 7-benzyloxy-N4-(2-methylpropyl)quinoline-3,4-diamine (29 g, 90 mmol) in 50:50 toluene:pyridine. The temperature of the reaction reached 40° C., and a precipitate formed. Triethylamine (15-20 g) and pyridine were added to help dissolve the precipitate. The reaction was heated at reflux for three hours and then allowed to cool to ambient temperature overnight. The solvents were removed under reduced pressure, and the black residue was dissolved in dichloromethane. The resulting solution was washed several times with aqueous sodium carbonate (150 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 29.2 g of 7-benzyloxy-2-ethoxymethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline as a tan solid.

Workup

  1. customreached 40° C.
  2. customa precipitate formed
  3. dissolutionto help dissolve the precipitate
  4. temperatureThe reaction was heated
  5. temperatureat reflux for three hours
  6. customThe solvents were removed under reduced pressure
  7. dissolutionthe black residue was dissolved in dichloromethane
  8. washThe resulting solution was washed several times with aqueous sodium carbonate (150 mL)
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a24e4274957a4416a553a9d1e3f94ae2
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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