HCID 21075716, compound → HCID 86594225, compound

HRID 1373930Notes

Reaction equation

HRID 1373930 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([NH2:18])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH3:2].C(O[CH:22](OCC)[CH2:23][CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])C>C(#N)C.C(O)(=O)C>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([N:18]=[CH:22][CH2:23][CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH3:2]

Participants

5

Reactant 2

HCID 21075716HCID 21075716, compoundHCID 71346567tert-Butyl (3,3-diethoxypropyl)carbamate

Product 1

HCID 86594225HCID 86594225, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-amine (1.00 g, 4.13 mmol) in 20 mL of acetonitrile and 5 mL of glacial acetic acid was treated with tert-butyl (3,3-diethoxypropyl)carbamate (2.55 g, 10.3 mmol) and heated to reflux under an atmosphere of nitrogen. After 15 h, the reaction mixture was concentrated under reduced pressure to yield a brown oil. The oil was partitioned between CHCl3 and saturated NaHCO3 solution and the phases were separated. The organic portion was washed with water (2×) and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield tert-butyl {3-[(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)imino]propyl}carbamate (1.64 g) as a dark red/orange oil.

Workup

  1. temperatureheated
  2. temperatureto reflux under an atmosphere of nitrogen
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customto yield a brown oil
  5. customThe oil was partitioned between CHCl3 and saturated NaHCO3 solution
  6. customthe phases were separated
  7. washThe organic portion was washed with water (2×) and brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-25bad26971ea4e9c84956ebfbcbe1bda
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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