Methane → tert-butyl 2-[2-(1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethylcarbamate

HRID 719236Notes

Reaction equation

HRID 719236 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH2:26](OC(OCC)OCC)C.Cl.[NH+]1C=CC=CC=1.C>C1(C)C=CC=CC=1.CO>[N:12]1([CH2:13][CH2:14][O:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:24])[CH3:23])[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=[CH:26]1

Participants

7

Reactant 4

HCID 297MethaneHCID 31214Ethyl orthoformateHCID 12106200Tert-butyl 2-{2-[(3-aminoquinolin-4-yl)amino]ethoxy)ethylcarbamateHCID 21584435Pyridinium hydrochloride

Product 1

HCID 21898035tert-butyl 2-[2-(1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethylcarbamateYield 73.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

A solution of tert-butyl 2-{2-[(3-aminoquinolin-4-yl)amino]ethoxy}ethylcarbamate (6.92 g, 20.0 mmol) in 100 mL of toluene was treated with triethylorthoformate (4.65 mL, 28.0 mmol) and the reaction mixture was heated to reflux. A 100 mg portion of pyridinium hydrochloride was then added and refluxing was continued for 2 h. The reaction was then concentrated to dryness under reduced pressure. The residue was dissolved in 200 mL of CH2Cl2 and washed with saturated NaHCO3, H2O and brine. The organic portion was dried over Na2SO4 and concentrated to give a green oil. The green oil was dissolved in 200 mL of hot MeOH and treated with 10 g of activated charcoal. The hot solution was filtered and concentrated to give 5.25 g of tert-butyl 2-[2-(1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethylcarbamate as a light yellow syrup.

Workup

  1. temperaturethe reaction mixture was heated to reflux
  2. temperaturerefluxing
  3. concentrationThe reaction was then concentrated to dryness under reduced pressure
  4. dissolutionThe residue was dissolved in 200 mL of CH2Cl2
  5. washwashed with saturated NaHCO3, H2O and brine
  6. dry with materialThe organic portion was dried over Na2SO4
  7. concentrationconcentrated
  8. customto give a green oil
  9. filtrationThe hot solution was filtered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-e27b52467d754176825feb9fa2355603
Source dataset
uspto-grants-2006_11
Patent number
US07132429B2

Reaction notes

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