Sodium Chloride → 3-Chloro-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

HRID 2097488Notes

Reaction equation

HRID 2097488 reaction equation
[CH3:1][Si:2]([CH3:18])([CH3:17])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:11]2[CH:12]=[N:13][NH:14][C:15](=[O:16])[C:10]=2[CH:9]=[CH:8]1.C(=O)([O-])O.[Na+].S([O-])(O)=O.[Na+].[Cl-:29].[Na+]>C(OCC)(=O)C.C(#N)C>[Cl:29][C:9]1[C:10]2[C:15](=[O:16])[NH:14][N:13]=[CH:12][C:11]=2[N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:18])([CH3:17])[CH3:1])[CH:8]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 23665763Sodium BisulfiteHCID 666030201-(2-Trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

Product 1

HCID 666026603-Chloro-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneYield 65%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 150 ml of acetonitrile solution containing 2.99 g (11.3 mmol) of 1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Reference example 16-(b) was added 1.42 g (10.6 mmol) of N-chlorosuccineimide, the mixture was stirred at room temperature for 3.5 hours, 0.53 g (4.0 mmol) of N-chlorosuccineimide was further added to the mixture and the resulting mixture was stirred for 24 hours. After completion of the reaction, to the reaction mixture were added a saturated aqueous solution of sodium hydrogencarbonate, 5% sodium hydrogen sulfite and ethyl acetate, and the mixture was stirred for 1 hour. Then, a saturated aqueous solution of sodium chloride was added to the solution and the liquids were separated. The organic layer after separation was further washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; toluene:ethyl acetate=9:1→7:3 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 2.20 g of the title compound as a white solid. (Yield: 65%)

Workup

  1. additionwas added 1.42 g (10.6 mmol) of N-chlorosuccineimide
  2. addition0.53 g (4.0 mmol) of N-chlorosuccineimide was further added to the mixture
  3. stirringthe resulting mixture was stirred for 24 hours
  4. customAfter completion of the reaction
  5. stirringthe mixture was stirred for 1 hour
  6. customthe liquids were separated
  7. customThe organic layer after separation
  8. washwas further washed with a saturated aqueous solution of sodium chloride
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. additionthe fractions containing the desired compound
  12. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-5815872e1a7c47c88d3ccbbc083e3312
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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