Hydrochloric Acid → TLR7/8 agonist 3

HRID 2180307Notes

Reaction equation

HRID 2180307 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:27][O:28][CH2:29][CH3:30])[N:14]([CH2:15][C:16]([NH:19]C(=O)OC(C)(C)C)([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.Cl>CCO>[NH2:19][C:16]([CH3:17])([CH3:18])[CH2:15][N:14]1[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:1])[C:11]=2[N:12]=[C:13]1[CH2:27][O:28][CH2:29][CH3:30]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22344420HCID 22344420, compound

Product 1

HCID 10380870TLR7/8 agonist 3Yield 84.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Tert-butyl 2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethylcarbamate (1.26 g, 3.05 mmol) was dissolved in 10 mL of EtOH and treated with 10 mL of 2 M HCl in EtOH. After heating at reflux for 2 h, the reaction mixture was cooled and concentrated under reduced pressure. The resulting yellow solid was dissolved in 50 mL of H2O and extracted with CHCl3 (20 mL). The organic layer was discarded and the aqueous portion was made basic (pH ˜12) by addition of concentrated NH4OH solution. This was then extracted with CHCl3 (4×20 mL) and the combined organic portions were dried with Na2SO4 and concentrated to give 1-(2-amino-2-methylpropyl)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinoline-4-amine (808 mg) as a light brown powder.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 2 h
  3. temperaturethe reaction mixture was cooled
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe resulting yellow solid was dissolved in 50 mL of H2O
  6. extractionextracted with CHCl3 (20 mL)
  7. additionby addition of concentrated NH4OH solution
  8. extractionThis was then extracted with CHCl3 (4×20 mL)
  9. dry with materialthe combined organic portions were dried with Na2SO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-1c4565c4c8f4460eb04a4dd16c2a2faf
Source dataset
uspto-grants-2005_05
Patent number
US06888000B2

Reaction notes

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