3-Methoxypropanoyl chloride → 2-(2-methoxyethyl)-1-[5-(methylthio)pentyl]-1H-imidazo[4,5-c]quinoline

HRID 897191

Reaction equation

HRID 897191 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[CH:11][C:10]=1[NH2:19].[CH3:20][O:21][CH2:22][CH2:23][C:24](Cl)=O>N1C=CC=CC=1>[CH3:20][O:21][CH2:22][CH2:23][C:24]1[N:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][S:2][CH3:1])[C:9]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[CH:11][C:10]=2[N:19]=1

Participants

4

Reactant 2

HCID 27597283-Methoxypropanoyl chlorideHCID 22320477N4-[5-(methylthio)pentyl]quinoline-3,4-diamine

Product 1

HCID 223204842-(2-methoxyethyl)-1-[5-(methylthio)pentyl]-1H-imidazo[4,5-c]quinolineYield 67.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

A round bottom flask was charged with a magnetic stir bar, N4-[5-(methylthio)pentyl]quinoline-3,4-diamine (3.56 g, 12.93 mmol) and anhydrous pyridine (52 mL) under a nitrogen atmosphere. The resulting homogeneous solution was cooled to 0° C. in an ice-water bath. To the cooled solution was added neat 3-methoxypropionyl chloride (2.74 g, 22.36 mmol). After addition of the acid chloride, the reaction was heated to reflux for 14 hours at which time the acylated intermediate was completely consumed. The solution was cooled and then partitioned between chloroform and saturated aqueous ammonium chloride. The layers were separated. The organic layer was washed with saturated aqueous sodium bicarbonate, dried over anhydrous sodium sulfate, filtered and then concentrated under reduced pressure to afford 2-(2-methoxyethyl)-1-[5-(methylthio)pentyl]-1H-imidazo[4,5-c]quinoline (3.0 g, 8.73 mmol) which was isolated as a brown oil and used without further purification.

Workup

  1. additionA round bottom flask was charged with a magnetic stir bar
  2. temperaturethe reaction was heated
  3. temperatureto reflux for 14 hours at which time the acylated intermediate
  4. customwas completely consumed
  5. temperatureThe solution was cooled
  6. custompartitioned between chloroform and saturated aqueous ammonium chloride
  7. customThe layers were separated
  8. washThe organic layer was washed with saturated aqueous sodium bicarbonate
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-51fcfc1161c2444f832104fe168ea856
Source dataset
uspto-grants-2005_07
Patent number
US06921826B2

Linked notes

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