1-[3-(Trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-ol → HCID 68499637, compound

HRID 2381079Notes

Reaction equation

[F:1][C:2]([F:20])([F:19])[C:3]1[N:7]2[N:8]=[C:9]([N:12]3[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14][CH2:13]3)[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1>[Pd].CO>[F:20][C:2]([F:1])([F:19])[C:3]1[N:7]2[N:8]=[C:9]([N:12]3[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14][CH2:13]3)[CH2:10][CH2:11][C:6]2=[N:5][N:4]=1

Participants

Conditions

Temperature: 50 °C

Procedure

1-[3-(Trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-ol (5 g, 17.41 mmol) and 5% palladium on carbon (50% wet, 0.963 g, 0.23 mmol) in MeOH (50 mL) were stirred under an atmosphere of hydrogen at 5 bar and 50° C. for 16 hours. The reaction was incomplete and further 5% palladium on carbon (50% wet, 0.963 g, 0.23 mmol) was added and the mixture was stirred at 50° C. for a further 16 hours. The catalyst was removed by filtration and washed with MeOH/DCM mixtures. The solvents were evaporated to give 1-[3-(trifluoromethyl)-7,8-dihydro-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-ol (4.93 g, 98%) as a solid.

Workup

customThe catalyst was removed by filtration
washwashed with MeOH/DCM mixtures
customThe solvents were evaporated

Sources & evidence

ORD record: ord-a3c95acaf6b34ab39e1a5fe0bfc48d63
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258140B2

Reaction notes

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