7-bromo-1-(4-chlorobutyl)-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline → thioacetic acid S-[4-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]ester

HRID 1818169Notes

Reaction equation

HRID 1818169 reaction equation
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].[Br:6][C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[N:19]([CH2:20][CH2:21][CH2:22][CH2:23]Cl)[C:18]([CH2:25][O:26][CH2:27][CH3:28])=[N:17][C:12]=3[CH:13]=[N:14][C:15]=2[CH:16]=1>CN(C=O)C>[Br:6][C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[N:19]([CH2:20][CH2:21][CH2:22][CH2:23][S:3][C:1](=[O:4])[CH3:2])[C:18]([CH2:25][O:26][CH2:27][CH3:28])=[N:17][C:12]=3[CH:13]=[N:14][C:15]=2[CH:16]=1

Participants

4

Reactant 2

HCID 219843887-bromo-1-(4-chlorobutyl)-2-ethoxymethyl-1H-imidazo[4,5-c]quinolineHCID 23670855Potassium ethanethioate

Product 1

HCID 86593762thioacetic acid S-[4-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]esterYield 103.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium thioacetate (1.70 g, 14.9 mmol) was added in one portion to a stirred solution of 7-bromo-1-(4-chlorobutyl)-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline (5.37 g, 13.5 mmol) in DMF (65 mL), and the reaction was stirred at ambient temperature for 21 hours. The DMF was removed under reduced pressure, and the residue was partitioned between dichloromethane (300 mL) and water (150 mL). The organic layer was separated, washed with brine (120 mL), dried over magnesium sulfate, filtered, and concentrated to provide 6.09 g of thioacetic acid S-[4-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]ester as a brown solid.

Workup

  1. customThe DMF was removed under reduced pressure
  2. customthe residue was partitioned between dichloromethane (300 mL) and water (150 mL)
  3. customThe organic layer was separated
  4. washwashed with brine (120 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d770395c64fd4f33b93cdccc915db921
Source dataset
uspto-grants-2009_10
Patent number
US07598382B2

Reaction notes

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