Ethanol → HCID 69507030, compound

HRID 2203554Notes

Reaction equation

HRID 2203554 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:26][O:27][CH2:28][CH3:29])[N:14]([CH2:15][C:16]([NH:19][C:20]([NH:22][CH:23]([CH3:25])[CH3:24])=[O:21])([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][NH:37]C(=O)OC(C)(C)C)=[CH:5][C:4]=2[N:3]=1.C(O)C>Cl>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:26][O:27][CH2:28][CH3:29])[N:14]([CH2:15][C:16]([NH:19][C:20]([NH:22][CH:23]([CH3:25])[CH3:24])=[O:21])([CH3:17])[CH3:18])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][NH2:37])=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 68898786Tert-butyl 6-{[4-amino-2-(ethoxymethyl)-1-(2-{[(isopropylamino)carbonyl]amino}-2-methylpropyl)-1h-imidazo[4,5-c]quinolin-7-yl]oxy}hexylcarbamate

Product 1

HCID 69507030HCID 69507030, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of tert-butyl 6-{[4-amino-2-(ethoxymethyl)-1-(2-{[(isopropylamino)carbonyl]amino}-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]oxy}hexylcarbamate (4.20 g, 6.84 mmol) in 3 M HCl in ethanol (50 mL, 150 mmol) was heated at reflux for five minutes, then was allowed to cool to room temperature and was concentrated under reduced pressure. The resulting orange solid was dissolved water and the solution was washed with dichloromethane (2×). The aqueous layer was treated with ammonium hydroxide until a basic pH was reached, then was extracted with dichloromethane (3×). The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated to yield 2.98 g of N-{2-[4-amino-7-[(6-aminohexyl)oxy]-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}-N′-isopropylurea as a dark orange solid.

Workup

  1. temperatureat reflux for five minutes
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionThe resulting orange solid was dissolved water
  4. washthe solution was washed with dichloromethane (2×)
  5. additionThe aqueous layer was treated with ammonium hydroxide until a basic pH
  6. extractionwas extracted with dichloromethane (3×)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-c0e49b1514b4413bada7015e5c49d42a
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

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