Hydrazine → HCID 66924743, compound

HRID 1962501Notes

Reaction equation

HRID 1962501 reaction equation
[C:1]1([C:7]2[NH:11][CH:10]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].C1OCCOCCOCCOCCOC1.Cl[C:35]1[N:40]=[N:39][C:38]([S:41](F)(=[O:43])=[O:42])=[CH:37][CH:36]=1.NN.C(=O)([O-])O.[Na+]>O1CCCC1>[C:1]1([C:7]2[N:11]([S:41]([C:38]3[N:39]=[N:40][CH:35]=[CH:36][CH:37]=3)(=[O:43])=[O:42])[CH:10]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 6

HCID 9321HydrazineHCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 516892Sodium BicarbonateHCID 10242379Ethyl 5-phenyl-1H-pyrrole-3-carboxylateHCID 107504176-Chloropyridazine-3-sulfonyl fluoride

Product 1

HCID 66924743HCID 66924743, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5-phenyl-1H-pyrrole-3-carboxylate (1.06 g) was dissolved in tetrahydrofuran (30 mL), sodium hydride (60% in oil, 300 mg) was added and the mixture was stirred at room temperature for 15 min. 15-Crown-5 (1.52 mL) was added and the mixture was further stirred at the same temperature for 15 min. 6-Chloropyridazine-3-sulfonyl fluoride (1.28 g) was added and the reaction mixture was stirred at room temperature for 30 min. Hydrazine (1.60 g) was added and the reaction mixture was stirred at room temperature for 15 min. Saturated aqueous sodium hydrogencarbonate solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (30 mL), manganese dioxide (75% chemically treated product, 5.0 g) was added, and the mixture was stirred at room temperature for 10 min. The reaction mixture was filtered through celite, and celite was washed with ethyl acetate. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→1:1) to give the title compound (yield 613 mg, yield 24% (containing impurity)).

Workup

  1. stirringthe mixture was further stirred at the same temperature for 15 min
  2. stirringthe reaction mixture was stirred at room temperature for 30 min
  3. stirringthe reaction mixture was stirred at room temperature for 15 min
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. dissolutionThe residue was dissolved in tetrahydrofuran (30 mL)
  9. additionmanganese dioxide (75% chemically treated product, 5.0 g) was added
  10. stirringthe mixture was stirred at room temperature for 10 min
  11. filtrationThe reaction mixture was filtered through celite, and celite
  12. washwas washed with ethyl acetate
  13. concentrationThe filtrate was concentrated under reduced pressure
  14. customthe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→1:1)

Sources & evidence

ORD record
ord-a40037bcb7314d1ebb183c7773677ad2
Source dataset
uspto-grants-2013_04
Patent number
US08415368B2

Reaction notes

Loading…