Hydrochloric Acid → HCID 58833621, compound

HRID 540897Notes

Reaction equation

HRID 540897 reaction equation
Cl.[NH2:2][C:3]1[C:12]2[N:13]=[C:14]([CH2:19][CH2:20][O:21][CH3:22])[N:15]([CH2:16][CH2:17][CH3:18])[C:11]=2[C:10]2[CH:9]=[CH:8][C:7]([O:23][CH2:24][CH2:25][CH2:26][NH:27]C(=O)OC(C)(C)C)=[CH:6][C:5]=2[N:4]=1.[OH-].[Na+]>C(O)C.O>[NH2:27][CH2:26][CH2:25][CH2:24][O:23][C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[N:15]([CH2:16][CH2:17][CH3:18])[C:14]([CH2:19][CH2:20][O:21][CH3:22])=[N:13][C:12]=3[C:3]([NH2:2])=[N:4][C:5]=2[CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58833668HCID 58833668, compound

Product 1

HCID 58833621HCID 58833621, compoundYield 69.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Concentrated hydrochloric acid (8.5 mL) was added to a solution of tert-butyl 3-{[4-amino-2-(2-methoxyethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-7-yl]oxy}propylcarbamate (prepared as described in Example 393, 12 g, 26 mmol) in ethanol (300 mL). The solution was heated at reflux for 4 hours. Upon cooling to ambient temperature a precipitate formed. The solid was isolated by filtration and the filtrate was evaporated to afford a white solid. The solids were combined and dissolved in water (40 mL). The solution was adjusted to approximately pH 12 with 50% aqueous sodium hydroxide and then was extracted with dichloromethane (4×250 mL). The organic layers were combined, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and evaporated to yield a solid that was purified by trituration in hot acetonitrile to provide 6.5 g of 7-(3-aminopropoxy)-2-(2-methoxyethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine as yellow crystals, mp 165-166.5° C.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 4 hours
  3. customformed
  4. customThe solid was isolated by filtration
  5. customthe filtrate was evaporated
  6. customto afford a white solid
  7. extractionwas extracted with dichloromethane (4×250 mL)
  8. washwashed with water and saturated aqueous sodium chloride
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customevaporated
  12. customto yield a solid
  13. customthat was purified by trituration in hot acetonitrile

Sources & evidence

ORD record
ord-0e0dfcf880074433a84d258b5192ade9
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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