4-(1-(3-(Trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl)piperidin-4-yl)phenol → 4-{1-[3-(Trifluoromethyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl}phenol

HRID 2381139Notes

Reaction equation

HRID 2381139 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[N:7]2[N:8]=[C:9]([N:12]3[CH2:17][CH2:16][CH:15]([C:18]4[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=4)[CH2:14][CH2:13]3)[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1>CO.[Pd]>[F:26][C:2]([F:1])([F:25])[C:3]1[N:7]2[N:8]=[C:9]([N:12]3[CH2:17][CH2:16][CH:15]([C:18]4[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=4)[CH2:14][CH2:13]3)[CH2:10][CH2:11][C:6]2=[N:5][N:4]=1

Participants

4

Reactant 1

HCID 367300784-(1-(3-(Trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl)piperidin-4-yl)phenol

Product 1

HCID 685004304-{1-[3-(Trifluoromethyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl}phenolYield 68.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-{1-[3-(Trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl}phenol (obtained as described in Example 5.2, preparation of starting materials) (30 g, 82.57 mmol) and 5% Pd on carbon (50% wet, JM Type 87L) (35.1 g, 8.26 mmol) in MeOH (50 mL) were stirred under an atmosphere of hydrogen at 5 bar and 50° C. for 5 days. The mixture was cooled to room temperature and the catalyst removed by filtration. The solvent was evaporated to give 4-{1-[3-(trifluoromethyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl}phenol (20.54 g, 68%).

Workup

  1. customthe catalyst removed by filtration
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-42878a0edfd14b0ca2f3100a635b0122
Source dataset
uspto-grants-2012_09
Patent number
US08258140B2

Reaction notes

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