Triethylamine → 8-benzyloxy-2-(2-methoxyethyl)-1-methyl-1H-imidazo[4,5-c]quinoline

HRID 2383134Notes

Reaction equation

HRID 2383134 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13]([NH2:19])=[C:12]2[NH:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:29][O:30][CH2:31][CH2:32][C:33](Cl)=O>ClCCl>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[N:15]=[CH:14][C:13]3[N:19]=[C:33]([CH2:32][CH2:31][O:30][CH3:29])[N:20]([CH3:21])[C:12]=3[C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27597283-Methoxypropanoyl chlorideHCID 670510076-(benzyloxy)-N4-methylquinoline-3,4-diamine

Product 1

HCID 670509718-benzyloxy-2-(2-methoxyethyl)-1-methyl-1H-imidazo[4,5-c]quinolineYield 38.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, a solution of 6-benzyloxy-N4-methylquinoline-3,4-diamine (7.88 g, 28.2 mmol), prepared as described in Parts A-F of Example 57, in dichloromethane (300 mL) was cooled to ˜0° C.; triethylamine (4.2 mL, 30.3 mmol) was added. Methoxypropionyl chloride (3.3 mL, 30.6 mmol) was added dropwise over a period of five minutes, and the reaction was stirred at ambient temperature for 90 minutes. The volatiles were removed under reduced pressure, and the residue was dissolved in ethanol (300 mL) and triethylamine (13 mL) and heated at 75° C. over two nights. The volatiles were removed under reduced pressure, and the residue was dissolved in chloroform. The resulting solution was washed with deionized water (3×200 mL) and concentrated under reduced pressure. Small volumes of hexanes and dichloromethane were added, and a white precipitate formed, which was isolated by filtration and washed with hexanes to provide 3.76 g of 8-benzyloxy-2-(2-methoxyethyl)-1-methyl-1H-imidazo[4,5-c]quinoline as a white solid.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. dissolutionthe residue was dissolved in ethanol (300 mL)
  3. temperaturetriethylamine (13 mL) and heated at 75° C. over two nights
  4. customThe volatiles were removed under reduced pressure
  5. dissolutionthe residue was dissolved in chloroform
  6. washThe resulting solution was washed with deionized water (3×200 mL)
  7. concentrationconcentrated under reduced pressure
  8. additionSmall volumes of hexanes and dichloromethane were added
  9. customa white precipitate formed
  10. customwhich was isolated by filtration
  11. washwashed with hexanes

Sources & evidence

ORD record
ord-9dee11abfd614ff39984185326763614
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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