Water → HCID 57515391, compound

HRID 44703Notes

Reaction equation

HRID 44703 reaction equation
N[C:2]1[C:11]2[N:12]=[C:13]([CH2:22][O:23][CH2:24][CH3:25])[N:14]([CH2:15][C:16]3([OH:21])[CH2:20][CH2:19][CH2:18][CH2:17]3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[H-].[Na+].I[CH3:29].O>C1COCC1>[CH2:24]([O:23][CH2:22][C:13]1[N:14]([CH2:15][C:16]2([O:21][CH3:29])[CH2:17][CH2:18][CH2:19][CH2:20]2)[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[CH:2][C:11]=2[N:12]=1)[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 57515381HCID 57515381, compound

Product 1

HCID 57515391HCID 57515391, compoundYield 24.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-{[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclopentanol (1.19 g, 3.66 mmol, prepared as described in Example 3) in THF (18 mL) at rt was added sodium hydride (60% dispersion in oil, 161 mg, 4.03 mmol). The mixture was stirred for 1 h and iodomethane (0.25 mL, 4.03 mmol) was added. The mixture was heated to 50° C. for 3 h and then was left to stand at rt overnight. More sodium hydride (60% dispersion in oil, 80 mg) and iodomethane (0.13 mL) were added. The mixture was heated for 2 h, then water was added and the mixture was extracted three times with ethyl acetate. The combined organic extracts were washed with brine and dried over Na2SO4, filtered and concentrated to an oil. The crude product was purified by flash chromatography (silica gel, eluted with ethyl acetate) to yield 2-(ethoxymethyl)-1-[(1-methoxycyclopentyl)methyl]-1H-imidazo[4,5-c]quinoline as a yellow oil (0.30 g, 24%).

Workup

  1. waitwas left
  2. waitto stand at rt overnight
  3. temperatureThe mixture was heated for 2 h
  4. extractionthe mixture was extracted three times with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to an oil
  9. customThe crude product was purified by flash chromatography (silica gel, eluted with ethyl acetate)

Sources & evidence

ORD record
ord-63cce99e4e9940f0ac0923e700a5089c
Source dataset
uspto-grants-2013_09
Patent number
US08541438B2

Reaction notes

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