Ammonia → Resiquimod

HRID 2119890Notes

Reaction equation

HRID 2119890 reaction equation
Cl[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])([CH3:18])[OH:17])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[NH3:24]>>[NH2:24][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])([CH3:18])[OH:17])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 22672652HCID 22672652, compound

Product 1

HCID 159603Resiquimod

Procedure

4-Chloro-α,α-dimethyl-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline-1-ethanol (1.0 g, 3 mmol, Example 100) and 7% methanolic ammonia (30 mL) were placed in a steel pressure vessel at about 150-160° C. for 6 hours. The vessel was cooled to below room temperature and the reaction solution removed and treated with methanolic potassium hydroxide. The solution was then evaporated to a low volume and diluted with water. The resulting precipitate was collected, washed with water and dried to provide 0.7 g of the crude product as a solid. The crude product was recrystallized from a mixture of ethyl acetate and methanol to provide a colorless solid.

Workup

  1. temperatureThe vessel was cooled to below room temperature
  2. customthe reaction solution removed
  3. additiontreated with methanolic potassium hydroxide
  4. customThe solution was then evaporated to a low volume
  5. additiondiluted with water
  6. customThe resulting precipitate was collected
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-2e691c04621445b6b0ada1e931c83551
Source dataset
uspto-grants-2004_02
Patent number
US06686472B2

Reaction notes

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