Tetrahydrofuran → HCID 68930143, compound

HRID 521286Notes

Reaction equation

HRID 521286 reaction equation
CON(C)C(=O)CCC[CH2:8][CH2:9][N:10]1[C:22]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[CH:14][C:13]=2[N:12]=[C:11]1[CH2:23][CH2:24][CH3:25].[CH3:28][Mg]Br.[CH2:31]1[CH2:35][O:34][CH2:33][CH2:32]1>C(Cl)(Cl)Cl.C(OCC)C>[CH2:23]([C:11]1[N:10]([CH2:9][CH2:8][CH2:33][CH2:32][CH2:31][C:35](=[O:34])[CH3:28])[C:22]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[CH:14][C:13]=2[N:12]=1)[CH2:24][CH3:25]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 86611632HCID 86611632, compoundHCID 178418573HCID 178418573, compound2×

Product 1

HCID 68930143HCID 68930143, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6212ChloroformSolvent

Procedure

To a solution of N-methoxy-N-methyl-6-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)hexanamide (22.0 g, 59.7 mmol) in chloroform (20 mL) and THF (200 mL) in an ice bath was added dropwise a solution of methylmagnesium bromide (40 mL of a 3 M solution in diethyl ether, 120 mmol). After 1 hour another charge of methylmagnesium bromide (40 mL of a 3 M solution in diethyl ether, 120 mmol) was added, the reaction mixture stirred at room temperature for 1 more hour and then quenched by the addition of a 10% solution of hydrochloric acid (about 10 mL). The mixture was concentrated under reduced pressure, the residue taken up in dichloromethane (200 mL), and the solution washed successively with a saturated aqueous sodium bicarbonate solution and brine (100 mL each), dried over potassium carbonate, and filtered. The solution was concentrated under reduced pressure and chromatographed on silica gel (elution with 3% methanol in dichloromethane) to provide 7-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)heptan-2-one (12.6 g) as an oil that was used directly in the next step without further purification.

Workup

  1. additionwas added
  2. customquenched by the addition of a 10% solution of hydrochloric acid (about 10 mL)
  3. concentrationThe mixture was concentrated under reduced pressure
  4. washthe solution washed successively with a saturated aqueous sodium bicarbonate solution and brine (100 mL each)
  5. dry with materialdried over potassium carbonate
  6. filtrationfiltered
  7. concentrationThe solution was concentrated under reduced pressure
  8. customchromatographed on silica gel (elution with 3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-e779156a120e4e568cbf68708d1c81f2
Source dataset
uspto-grants-2016_05
Patent number
US09328110B2

Reaction notes

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