Dimethyl Sulfate → HCID 66811718, compound

HRID 2063278Notes

Reaction equation

HRID 2063278 reaction equation
[OH:1][CH:2]1[CH2:9][N:8]2[C:4](=[N:5][C:6]3[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:7]=32)[CH2:3]1.[H-].[Na+].S(OC)(O[CH3:23])(=O)=O>O1CCCC1.O>[CH3:23][O:1][CH:2]1[CH2:9][N:8]2[C:4](=[N:5][C:6]3[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:7]=32)[CH2:3]1

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 66811769HCID 66811769, compound

Product 1

HCID 66811718HCID 66811718, compoundYield 23.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.28 g (1.28 mmol) of 2,3-dihydro-2-hydroxy-6-nitro-1H-pyrrolo[1,2-a]benzimidazole (step IX-2 of Example IX) in 5 ml of tetrahydrofuran is added to a suspension, stirred under argon at 20° C., of 0.2 g (5 mmol) of sodium hydride at 60% in 10 ml of tetrahydrofuran. After stirring for fifteen minutes, 0.24 ml (2.5 mmol) of dimethyl sulphate is added. The reaction mixture is stirred at 20° C. for 12 hours and then poured in 100 ml of water and extracted three times with 50 ml of ethyl acetate. The organic phases are combined, washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulphate and concentrated under reduced pressure. The residue obtained is purified by silica column chromatography, elution being carried out with a mixture of dichloromethane and methanol. 70 mg of the expected product are thus isolated in the form of a foam.

Workup

  1. stirringThe reaction mixture is stirred at 20° C. for 12 hours
  2. extractionextracted three times with 50 ml of ethyl acetate
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. customis purified by silica column chromatography, elution
  8. additionbeing carried out with a mixture of dichloromethane and methanol

Sources & evidence

ORD record
ord-f4e5409105be4285ab55a6bbc8326d0d
Source dataset
uspto-grants-2012_10
Patent number
US08288376B2

Reaction notes

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