2-Nitropropane → HCID 86627042, compound

HRID 2097505Notes

Reaction equation

HRID 2097505 reaction equation
[N+](C(C)C)([O-])=[O:2].C(O)C.[O-]CC.[Na+].[Br:14][C:15]1[N:24]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:18]2[CH:19]=[N:20][NH:21][C:22](=[O:23])[C:17]=2[C:16]=1[CH2:33]Br>C(O)C>[Br:14][C:15]1[N:24]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:18]2[CH:19]=[N:20][NH:21][C:22](=[O:23])[C:17]=2[C:16]=1[CH:33]=[O:2]

Participants

5

Reactant 3

HCID 3982-NitropropaneHCID 23706232Ethanol sodium ethoxideHCID 66602907HCID 66602907, compound

Product 1

HCID 86627042HCID 86627042, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 370 mg (4.2 mmol) of 2-nitropropane were added 10 ml of dehydrated ethanol and 1.43 g (4.2 mmol) of 20% sodium ethoxide ethanol solution, then, 500 mg (0.84 mmol) of 2-bromo-3-bromomethyl-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Reference example 24-(f) was added to the mixture at 5° C., and the mixture was stirred at the same temperature for 1 hour. After completion of the reaction, ice water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer after separation was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=1:1 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 167 mg of the title compound as a white solid. (Yield: 32%)

Workup

  1. addition24-(f) was added to the mixture at 5° C.
  2. additionwas added to the reaction mixture
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe organic layer after separation
  5. washwas washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. additionthe fractions containing the desired compound
  9. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-79fa2112b15c42aa87e527db5a621b4b
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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