Tert-butyl (2-{[1-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-oxo-2-phenylethyl]amino}-2-oxoethyl)carbamate → HCID 178456633, Verbindung

HRID 915052

Reaktionsgleichung

Reaktionsgleichung von HRID 915052
[CH:1]([N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([CH:11]([NH:20][C:21](=[O:31])[CH2:22][NH:23]C(=O)OC(C)(C)C)[C:12](=O)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:5]1)([CH3:3])[CH3:2]>Cl.CO.N1C=CC=CC=1>[OH:31][C:21]1[N:20]=[C:11]([C:6]2[CH:7]=[CH:8][C:9](=[O:10])[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=2)[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:23][CH:22]=1

Komponenten

5

Edukt 1

HCID 86600908Tert-butyl (2-{[1-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-oxo-2-phenylethyl]amino}-2-oxoethyl)carbamate

Produkt 1

HCID 178456633HCID 178456633, VerbindungAusbeute 29,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
82.5 °C

Versuchsvorschrift

A solution of tert-butyl (2-{[1-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-oxo-2-phenylethyl]amino}-2-oxoethyl)carbamate (310 mg) in 10% hydrogen chloride in MeOH (3 ml) was stirred at 20-25° C. for 18 hours and the mixture was concentrated under reduced pressure to give a residue. The residue was dissolved in pyridine (1.5 ml) and heated at 80-85° C. for 10 hours. After evaporation of pyridine, the mixture was dissolved in CHCl3, washed with 1N HCl, sat. aq. NaHCO3 and brine, dried over MgSO4 and concentrated under reduced pressure to give syrup. The syrup was purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (40:60 v/v) to give 6-(6-hydroxy-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone as a solid (65 mg).

Aufarbeitung

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customto give a residue
  3. customAfter evaporation of pyridine
  4. dissolutionthe mixture was dissolved in CHCl3
  5. washwashed with 1N HCl, sat. aq. NaHCO3 and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customto give syrup
  9. customThe syrup was purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (40:60 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-6dcc2126a1a142d8914a67b900e8af3f
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265120B2

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