Hydrochloric Acid → 4-amino-2-ethoxymethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-ol

HRID 598348Notes

Reaction equation

HRID 598348 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][O:21][CH2:22][CH3:23])[N:14]([CH2:15][C:16]([CH3:19])([OH:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([O:24]CC3C=CC=CC=3)=[CH:5][C:4]=2[N:3]=1.Cl>C(=O)([O-])[O-].[Na+].[Na+]>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][O:21][CH2:22][CH3:23])[N:14]([CH2:15][C:16]([OH:18])([CH3:19])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([OH:24])=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57545343(4-amino-7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol

Product 1

HCID 1363405384-amino-2-ethoxymethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-ol

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent2×

Procedure

(4-Amino-7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol was debenzylated using the general method of Example 5. Upon completion of the reaction, the catalyst was removed by filtration through a polytetrafluoroethylene (PTFE) membrane and the filtrate was concentrated under reduced pressure to give a tan solid. The solid was slurried in 1% aqueous sodium carbonate. This formed a gooey slurry. The pH was lowered to 1 with the addition of concentrated hydrochloric acid. When a homogenous solution was formed, the pH was adjusted back to 5 with the addition of 1% aqueous sodium carbonate. A solid precipitated and was collected by filtration. The solid was dried under a stream of air to give 4-amino-2-ethoxymethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-ol as an off-white solid.

Workup

  1. customUpon completion of the reaction
  2. customthe catalyst was removed by filtration through a polytetrafluoroethylene (PTFE) membrane
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto give a tan solid
  5. customThis formed a gooey slurry
  6. customWhen a homogenous solution was formed
  7. customA solid precipitated
  8. filtrationwas collected by filtration
  9. customThe solid was dried under a stream of air

Sources & evidence

ORD record
ord-37ac15cd85684669adaaed7c08f8d1e2
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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