Ethyl orthoformate → 1-{2-[2-(methylsulfonyl)ethoxy]ethyl}-1H-imidazo[4,5-c]quinoline

HRID 547292Notes

Reaction equation

HRID 547292 reaction equation
[CH:1](OCC)(OCC)OCC.[CH3:11][S:12]([CH2:15][CH2:16][O:17][CH2:18][CH2:19][NH:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=[CH:23][C:22]=1[NH2:31])(=[O:14])=[O:13].Cl.N1C=CC=CC=1>C(#N)C>[CH3:11][S:12]([CH2:15][CH2:16][O:17][CH2:18][CH2:19][N:20]1[C:21]2[C:30]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[N:24]=[CH:23][C:22]=2[N:31]=[CH:1]1)(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 10176127Pyridinium chlorideHCID 86064731N4-{2-[2-(methylsulfonyl)ethoxy]ethyl}quinoline-3,4-diamine

Product 1

HCID 672027231-{2-[2-(methylsulfonyl)ethoxy]ethyl}-1H-imidazo[4,5-c]quinolineYield 67.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triethyl orthoformate (2 mL, 12 mmol) was added to a stirred solution of N4-{2-[2-(methylsulfonyl)ethoxy]ethyl}quinoline-3,4-diamine (3.1 g, 10 mmol) in acetonitrile (50 mL). Pyridine hydrochloride (0.3 g) was added and the reaction mixture was heated to reflux with the volatiles being collected in a Dean Stark trap. After 20 minutes analysis by TLC indicated that the starting material was consumed. The reaction mixture was concentrated under reduced pressure to provide a viscous oil. The oil was triturated with ethyl acetate. The resulting solid was isolated by filtration and washed with ethyl acetate to provide 2.17 g of 1-{2-[2-(methylsulfonyl)ethoxy]ethyl}-1H-imidazo[4,5-c]quinoline as an off-white powder.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux with the volatiles
  3. custombeing collected in a Dean Stark trap
  4. customwas consumed
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. customto provide a viscous oil
  7. customThe oil was triturated with ethyl acetate
  8. customThe resulting solid was isolated by filtration
  9. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-1d9a4c40b50c4514a994640384869fb7
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

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