Triethylamine → 2-[(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)oxy]acetamide

HRID 2105500Notes

Reaction equation

HRID 2105500 reaction equation
[CH2:1]([C:4]1[N:5]([OH:17])[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:16]=1)[CH2:2][CH3:3].Br[CH2:19][C:20]([NH2:22])=[O:21].C(N(CC)CC)C>C1COCC1>[CH2:1]([C:4]1[N:5]([O:17][CH2:19][C:20]([NH2:22])=[O:21])[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:16]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 696322-BromoacetamideHCID 675069482-propyl-1H-imidazo[4,5-c]quinolin-1-ol

Product 1

HCID 675069802-[(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)oxy]acetamideYield 83.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-propyl-1H-imidazo[4,5-c]quinolin-1-ol (2.0 g, 8.8 mmol), bromoacetamide (1.9 g, 14 mmol), and triethylamine (2.8 mL, 0.020 mol) in THF (100 mL) was heated at reflux overnight. The solvent was removed under reduced pressure, and dichloromethane (75 mL) and saturated aqueous sodium bicarbonate (25 mL) were added to the residue. The resulting mixture was filtered to provide 2.1 g of 2-[(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)oxy]acetamide as a solid. The organic layer was separated, and methanol was added until all solids were dissolved. The solution was then dried over potassium carbonate, filtered, and concentrated under reduced pressure to provide an additional 0.13 g of material.

Workup

  1. temperatureat reflux overnight
  2. customThe solvent was removed under reduced pressure, and dichloromethane (75 mL) and saturated aqueous sodium bicarbonate (25 mL)
  3. additionwere added to the residue
  4. filtrationThe resulting mixture was filtered

Sources & evidence

ORD record
ord-cb390c5089a544359f5c8a94ea2b5417
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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