Water → HCID 67255495, compound

HRID 1672354Notes

Reaction equation

HRID 1672354 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[NH:12][C:13](=[O:22])[N:14]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[Cl:21])[C:5]=3[C:4]=2[CH:3]=1.[H-].[Na+].[CH3:25]I.O>CN(C)C=O>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([CH3:25])[C:13](=[O:22])[N:14]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[Cl:21])[C:5]=3[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67255446HCID 67255446, compound

Product 1

HCID 67255495HCID 67255495, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

300 mg (0.8 mmol) of 8-bromo-1-(2-chloro-phenyl)-1,3-dihydro-imidazo[4,5-c]quinolin-2-one [see under B)] are dissolved in 5 ml of anhydrous N,N-dimethylformamide and 35 mg (0.8 mmol) of NaH are added portionwise. The suspension is stirred for 90 min at room temperature and 113 mg (0.8 mmol) of methyl iodide dissolved in 3 ml of N,N-dimethylformamide are added. After stirring for 18 h at room temperature, the solution is cooled at 0° C. and 20 ml of water are added slowly to the stirred suspension. The suspension is extracted with ethyl acetate and the water phase is discarded. The organic phase is washed with brine, dried with Na2SO4 and evaporated to dryness. The crude compound is purified by flash-chromatography (dichloromethane with 2% methanol) to provide the title compound: Analytical HPLC: tret=7.64 min (Grad. 2); ES-MS: m/e0=388.0, 390.0.

Workup

  1. additionare added
  2. stirringAfter stirring for 18 h at room temperature
  3. temperaturethe solution is cooled at 0° C.
  4. extractionThe suspension is extracted with ethyl acetate
  5. washThe organic phase is washed with brine
  6. dry with materialdried with Na2SO4
  7. customevaporated to dryness
  8. customThe crude compound is purified by flash-chromatography (dichloromethane with 2% methanol)

Sources & evidence

ORD record
ord-d5cd2018f8d64805979ab9eac2921bf3
Source dataset
uspto-grants-2011_08
Patent number
US07998972B2

Reaction notes

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