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 517818Notes

Reaction equation

HRID 517818 reaction equation
[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

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

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:

Workup

  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

Sources & evidence

ORD record
ord-24d36e55a3634928a611084a77e601cb
Source dataset
uspto-grants-2015_08
Patent number
US09115134B2

Reaction notes

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