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

HRID 547290Notes

Reaction equation

HRID 547290 reaction equation
[C:1](OC)(OC)(OC)[CH2:2][CH2:3][CH2:4][CH3:5].[CH3:12][S:13]([CH2:16][CH2:17][O:18][CH2:19][CH2:20][NH:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]=[CH:24][C:23]=1[NH2:32])(=[O:15])=[O:14].Cl.N1C=CC=CC=1>C(#N)C>[CH2:2]([C:1]1[N:21]([CH2:20][CH2:19][O:18][CH2:17][CH2:16][S:13]([CH3:12])(=[O:15])=[O:14])[C:22]2[C:31]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[N:25]=[CH:24][C:23]=2[N:32]=1)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 83755Trimethyl orthovalerateHCID 10176127Pyridinium chlorideHCID 86064731N4-{2-[2-(methylsulfonyl)ethoxy]ethyl}quinoline-3,4-diamine

Product 1

HCID 672036432-butyl-1-{2-[2-(methylsulfonyl)ethoxy]ethyl}-1H-imidazo[4,5-c]quinolineYield 100.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Trimethyl orthovalerate (1.3 g, 8.1 mmol) was added to a solution of N4-{2-[2-(methylsulfonyl)ethoxy]ethyl}quinoline-3,4-diamine (˜2.3 g, ˜7.4 mmol) in acetonitrile (37 mL). Pyridine hydrochloride (˜100 mg) was added and the reaction mixture was heated to reflux with the volatiles being collected in a Dean Stark trap. After 15 minutes analysis by TLC indicated that the starting material was consumed. The reaction mixture was cooled and then concentrated under reduced pressure to provide ˜2.8 g of 2-butyl-1-{2-[2-(methylsulfonyl)ethoxy]ethyl}-1H-imidazo[4,5-c]quinoline as a greenish-yellow 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. temperatureThe reaction mixture was cooled
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8f87bbdc25a94b5a88391ee4b48fae16
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

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