Water → HCID 11475554, compound

HRID 540809Notes

Reaction equation

HRID 540809 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:19][CH2:20][CH3:21])[N:14]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([OH:22])=[CH:5][C:4]=2[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:30][C:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:32].O>CN(C=O)C>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:19][CH2:20][CH3:21])[N:14]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([O:22][CH2:30][C:31]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:32])=[CH:5][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6259Phenacyl bromide2×HCID 10796Cesium carbonateHCID 135531151HCID 135531151, compound

Product 1

HCID 11475554HCID 11475554, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A warm solution of 4-amino-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-7-ol (266 mg, 0.891 mmol) in DMF (20 mL) was cooled to approximately 0° C. Solid cesium carbonate (580 mg, 1.78 mmol) was added. After ten minutes, 2-bromoacetophenone (186 mg, 0.935 mmol) was added in one portion, and the reaction was allowed to warm to room temperature and was stirred overnight. An analysis by high-performance liquid chromatography (HPLC) indicated the presence of starting material. Additional 2-bromoacetophenone was added, and the reaction was stirred for six hours. The reaction was poured into deionized water (200-300 mL) and stirred for 15 hours. The resulting precipitate was isolated by filtration and purified by column chromatography on silica gel (eluting with chloroform:methanol ranging in ratios from 99.5:0.5 to 98:2). The product was then recrystallized from acetonitrile, isolated by filtration, and dried overnight under high vacuum to provide 222 mg of 2-(4-amino-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-7-yloxy)-1-phenylethanone as white crystals, mp 178.0-180.0° C.

Workup

  1. waitAfter ten minutes
  2. stirringthe reaction was stirred for six hours
  3. stirringstirred for 15 hours
  4. customThe resulting precipitate was isolated by filtration
  5. custompurified by column chromatography on silica gel (eluting with chloroform:methanol ranging in ratios from 99.5:0.5 to 98:2)
  6. customThe product was then recrystallized from acetonitrile
  7. customisolated by filtration
  8. customdried overnight under high vacuum

Sources & evidence

ORD record
ord-3165c1623d964f53a9240f8ab9a7ba02
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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