6-Chloro-7-cyclobutyl-3-phenyl-1,2,4-triazolo[4,3-b]pyridazine → N-(7-Cyclobutyl-3-phenyl-1,2,4-triazolo[4,3-b]pyridazin-6-yl)-N-(1-methyl-1H-1,2,4-triazol-3-ylmethyl)amine

HRID 277329

Reaktionsgleichung

Reaktionsgleichung von HRID 277329
Cl[C:2]1[C:3]([CH:17]2[CH2:20][CH2:19][CH2:18]2)=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:9][N:10]=2)[N:7]=1.Cl.[CH3:22][N:23]1[CH:27]=[N:26][C:25]([CH2:28][NH2:29])=[N:24]1>C(N(CC)CC)C.CN(C=O)C>[CH:17]1([C:3]2[C:2]([NH:29][CH2:28][C:25]3[N:26]=[CH:27][N:23]([CH3:22])[N:24]=3)=[N:7][N:6]3[C:8]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)=[N:9][N:10]=[C:5]3[CH:4]=2)[CH2:20][CH2:19][CH2:18]1

Komponenten

5

Edukt 2

HCID 110005936-Chloro-7-cyclobutyl-3-phenyl-1,2,4-triazolo[4,3-b]pyridazineHCID 18314526(1-methyl-1H-1,2,4-triazol-3-yl)methanamine hydrochloride

Produkt 1

HCID 9841820N-(7-Cyclobutyl-3-phenyl-1,2,4-triazolo[4,3-b]pyridazin-6-yl)-N-(1-methyl-1H-1,2,4-triazol-3-ylmethyl)amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 6-chloro-7-cyclobutyl-3-phenyl-1,2,4-triazolo[4,3-b]pyridazine (144 mg, 0.52 mmol) and C-(1-methyl-1H-1,2,4-triazol-3-yl)methylamine hydrochloride (300 mg, 2.0 mmol) in triethylamine (1 ml) and dry DMF (1 ml) was stirred and heated at 100° C. in a sealed tube for 20 hours. Upon cooling the volatiles were removed in vacuo, and the residue was partitioned between dichloromethane and saturated aqueous sodium hydrogen carbonate. The aqueous was further extracted with dichloromethane (x2). The combined extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatograhy on silica gel, eluting with 2%→5%→10% methanol-dichloromethane to give, in order of elution:

Aufarbeitung

  1. temperatureUpon cooling the volatiles
  2. customwere removed in vacuo
  3. customthe residue was partitioned between dichloromethane and saturated aqueous sodium hydrogen carbonate
  4. extractionThe aqueous was further extracted with dichloromethane (x2)
  5. dry with materialThe combined extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by chromatograhy on silica gel
  9. washeluting with 2%→5%→10% methanol-dichloromethane
  10. customto give, in order of elution

Quellen und Nachweise

ORD-Eintrag
ord-5d6990ded6be4a6689857b1bd2ee51ae
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355798B1

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