Ammonia → HCID 59574209, compound

HRID 2092033Notes

Reaction equation

HRID 2092033 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.[O:9]=[C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[N:11]1[CH:20]([CH2:24][CH3:25])C(O)=O.FC(F)(F)C(O)=O.N>O.[N+]([O-])([O-])=O.[Ag+].C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:8])=[CH:6][C:7]=1[CH:20]([N:11]1[C:12](=[O:19])[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]1=[O:9])[CH2:24][CH3:25]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 673313,6-DichloropyridazineHCID 3442562-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)butanoic acid

Product 1

HCID 59574209HCID 59574209, compound

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

3,6-Dichloropyridazine (596 mg, 4 mmol), 2-(1,3-dioxoisoindolin-2-yl)butanoic acid (1.59 g, 6.8 mmol), silver nitrate (67.9 mg, 0.4 mmol), trifluoroacetic acid (91.2 mg, 0.8 mmol) and water (10 mL) were heated at 70° C. with stirring, and to the resulting mixture, diammonium peroxodisulfate (1.64 g, 7.2 mmol) in water (2 mL) was added dropwise over 30 minutes. After the dropwise addition, the resulting reaction mixture was stirred at 70° C. for 30 minutes, then mixed with 10 mL of ethyl acetate and allowed to cool to room temperature. The reaction mixture was cooled with ice, then basified with 28% aqueous ammonia (to pH 9) and extracted with ethyl acetate. The resulting organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform/ethyl acetate=1/1) to give a crude product, which was used for the next reaction.

Workup

  1. additionAfter the dropwise addition
  2. customthe resulting reaction mixture
  3. stirringwas stirred at 70° C. for 30 minutes
  4. temperatureThe reaction mixture was cooled with ice
  5. extractionextracted with ethyl acetate
  6. washThe resulting organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated under reduced pressure
  9. customThe resulting residue was purified by silica gel column chromatography (chloroform/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-2514f879782a4a9da329e78f392b9efc
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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