Sodium Methoxide → HCID 57853904, compound

HRID 415473Notes

Reaction equation

HRID 415473 reaction equation
[CH2:1]([N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[C:12]([NH2:21])[C:11]=2[N:10]=[C:9]1S(C)(=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][O-:27].[Na+]>CO>[CH2:1]([N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[C:12]([NH2:21])[C:11]=2[N:10]=[C:9]1[O:27][CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 66623176HCID 66623176, compound

Product 1

HCID 57853904HCID 57853904, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 1-benzyl-2-(methylsulfonyl)-1H-imidazo[4,5-c]quinolin-4-amine (890 mg, 2.5 mmol) in methanol (10 mL) was stirred at room temperature for two minutes, and sodium methoxide (5 mL of a 25% w/w solution in methanol) was added. The resulting suspension was stirred at room temperature for one hour and then concentrated under reduced pressure. The residue was partitioned between ethyl acetate (200 mL) and water (150 mL). The organic layer was separated and dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by automated flash chromatography (silica cartridge, eluting with aqueous ammonium hydroxide:methanol:dichloromethane in a gradient from 0:0:100 to 0.3:4.7:95). The resulting off-white solid was triturated with hot acetonitrile, isolated by filtration, and dried under vacuum to provide 50 mg of 1-benzyl-2-methoxy-1H-imidazo[4,5-c]quinolin-4-amine as a white solid, mp 240-242° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate (200 mL) and water (150 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by automated flash chromatography (silica cartridge
  8. washeluting with aqueous ammonium hydroxide
  9. customThe resulting off-white solid was triturated with hot acetonitrile
  10. customisolated by filtration
  11. customdried under vacuum

Sources & evidence

ORD record
ord-e76388e430ba4a22a684b4127f648197
Source dataset
uspto-grants-2012_01
Patent number
US08088790B2

Reaction notes

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