Dimethylformamide → HCID 86051826, compound

HRID 2426349Notes

Reaction equation

HRID 2426349 reaction equation
[CH3:1][CH:2]([CH3:17])[CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:6]=[CH:5]1.C([Li])CCC.CN([CH:26]=[O:27])C>O1CCCC1>[CH3:1][CH:2]([CH3:17])[CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:6]=[C:5]1[CH:26]=[O:27]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11424651DeaminoimiquimodHCID 178418339Butyllithium

Product 1

HCID 86051826HCID 86051826, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline (U.S. Pat. No. 5,175,296 Example 1 Part C, 25.64 g, 113.8 mmol) in tetrahydrofuran (THF) (450 mL) was cooled to −78° C. Butyllithium (45.5 mL of a 2.5 M solution in hexanes) was added dropwise over a period of ten minutes, and the resulting solution was stirred for ten minutes. DMF (20.1 mL, 274.4 mmol) was added, and the reaction was allowed to warm to room temperature and stirred for one hour. The THF was then removed under reduced pressure, and the residue was dissolved in ethyl acetate (400 mL). The resulting solution was washed with brine (400 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting sequentially with 0.5% and 1% methanol in dichloromethane) to provide 10.5 g of 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2-carbaldehyde as a light brown solid.

Workup

  1. stirringstirred for one hour
  2. customThe THF was then removed under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate (400 mL)
  4. washThe resulting solution was washed with brine (400 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by column chromatography on silica gel (
  9. washeluting sequentially with 0.5% and 1% methanol in dichloromethane)

Sources & evidence

ORD record
ord-8a0444cfdb01418b855b8004fae434f6
Source dataset
uspto-grants-2011_06
Patent number
US07968563B2

Reaction notes

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