tert-Butyl {4-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-ylmethyl]benzyl}carbamate → 1-(4-aminomethylbenzyl)-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine

HRID 9494Notes

Reaction equation

HRID 9494 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:31][O:32][CH2:33][CH3:34])[N:14]([CH2:15][C:16]3[CH:30]=[CH:29][C:19]([CH2:20][NH:21]C(=O)OC(C)(C)C)=[CH:18][CH:17]=3)[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([C:35]3[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=3)=[CH:5][C:4]=2[N:3]=1>Cl>[NH2:21][CH2:20][C:19]1[CH:29]=[CH:30][C:16]([CH2:15][N:14]2[C:10]3[C:9]4[CH:8]=[CH:7][C:6]([C:35]5[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=5)=[CH:5][C:4]=4[N:3]=[C:2]([NH2:1])[C:11]=3[N:12]=[C:13]2[CH2:31][O:32][CH2:33][CH3:34])=[CH:17][CH:18]=1

Participants

3

Reactant 1

HCID 86593769tert-Butyl {4-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-ylmethyl]benzyl}carbamate

Product 1

HCID 219840501-(4-aminomethylbenzyl)-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amineYield 97.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

tert-Butyl {4-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-ylmethyl]benzyl}carbamate (0.660 g) was added to ethanolic hydrogen chloride (4M, 10 mL) and the solution was heated at reflux temperature for 30 minutes. The reaction was cooled to room temperature and concentrated under reduced pressure. Diethyl ether and water were added to the oily residue and the layers were separated. The aqueous fraction was brought to pH 13 with 10% aqueous sodium hydroxide and then extracted sequentially with dichloromethane and dichloromethane containing 5% methanol. The organic fractions were combined, washed sequentially with water and saturated aqueous sodium chloride, dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield 0.526 g of 1-(4-aminomethylbenzyl)-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine as an off-white solid, mp 211.0–213.5° C.

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux temperature for 30 minutes
  3. concentrationconcentrated under reduced pressure
  4. additionDiethyl ether and water were added to the oily residue
  5. customthe layers were separated
  6. extractionextracted sequentially with dichloromethane and dichloromethane containing 5% methanol
  7. washwashed sequentially with water and saturated aqueous sodium chloride
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4c2681be703e4a42a213e914545c842e
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

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