Dimethylformamide → HCID 86051826, compound

HRID 599451Notes

Reaction equation

HRID 599451 reaction equation
C([Li])CCC.[CH3:6][CH:7]([CH3:22])[CH2:8][N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[N:11]=[CH:10]1.CN([CH:26]=[O:27])C>O1CCCC1>[CH3:6][CH:7]([CH3:22])[CH2:8][N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[N:11]=[C:10]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 n-butyllithium in hexanes (2.5 M, 45.5 mL, 1.15 equivalents) was added dropwise to a stirred, −78° C. solution of 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline (prepared as described in Example 32 of U.S. Pat. No. 4,689,338, 25.64 g) in tetrahydrofuran (450 mL). The solution was stirred for 10 minutes, then DMF (20.1 mL, 2.3 equivalents) was added. The reaction mixture was allowed to warm to room temperature over 1 hour. The volatiles were removed under reduced pressure and the residue was portioned between ethyl acetate (400 mL) and brine (400 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield a brown solid that was purified by flash chromatography (silica gel, gradient elution with 0.5-1% methanol in dichloromethane) to provide 10.5 g of 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2-carbaldehyde.

Workup

  1. customprepared
  2. customThe volatiles were removed under reduced pressure
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto yield a brown solid that
  7. customwas purified by flash chromatography (silica gel, gradient elution with 0.5-1% methanol in dichloromethane)

Sources & evidence

ORD record
ord-fcde626bc39344ce91b21898d61e532f
Source dataset
uspto-grants-2011_03
Patent number
US07897767B2

Reaction notes

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