3-Chloro-6-(4-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine → 3-Chloro-6-(4-fluorophenyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazine

HRID 517818

Reaktionsgleichung

Reaktionsgleichung von HRID 517818
[Cl:1][C:2]1[N:6]2[N:7]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1>C(O)(=O)C.[Zn]>[Cl:1][C:2]1[N:6]2[N:7]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[CH2:9][CH2:10][C:5]2=[N:4][N:3]=1

Komponenten

4

Edukt 1

HCID 446043783-Chloro-6-(4-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine

Produkt 1

HCID 675246973-Chloro-6-(4-fluorophenyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazineAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

790 mg of zinc powder are added to a mixture of 300 mg of 3-chloro-6-(4-fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazine in 10 cm3 of glacial acetic acid at 20° C. After stirring for 1 h, the suspension is filtered and the filtrate is concentrated to dryness under vacuum. The oily residue is purified by dry deposit on Biotage Quad 12M (KP-SIL, 60 Å; 32-63 μm), elution being carried out with a 95:5 mixture of dichloromethane/methanol. 263 mg of 3-chloro-6-(4-fluorophenyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazine are thus obtained in the form of a yellowy-brown powder, the characteristics of which are as follows:

Aufarbeitung

  1. filtrationthe suspension is filtered
  2. concentrationthe filtrate is concentrated to dryness under vacuum
  3. customThe oily residue is purified
  4. customby dry deposit
  5. washon Biotage Quad 12M (KP-SIL, 60 Å; 32-63 μm), elution
  6. additionbeing carried out with a 95:5 mixture of dichloromethane/methanol

Quellen und Nachweise

ORD-Eintrag
ord-24d36e55a3634928a611084a77e601cb
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115134B2

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