HCID 59149722, compound → HCID 59149830, compound

HRID 1675124Notes

Reaction equation

HRID 1675124 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[N:7]2[N:8]=[C:9]([N:12]3[CH2:17][CH:16]=[C:15]([C:18]4[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=4)[CH2:14][CH2:13]3)[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1>[Pd].CO>[N:20]1[CH:21]=[CH:22][CH:23]=[C:18]([CH:15]2[CH2:16][CH2:17][N:12]([C:9]3[CH:10]=[CH:11][C:6]4[N:7]([C:3]([C:2]([F:25])([F:1])[F:24])=[N:4][N:5]=4)[N:8]=3)[CH2:13][CH2:14]2)[CH:19]=1

Participants

4

Reactant 1

HCID 59149722HCID 59149722, compound

Product 1

HCID 59149830HCID 59149830, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1′-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]-1′,2′,3′,6′-tetrahydro-3,4′-bipyridine (obtained as described in Example 605) (82 mg, 0.24 mmol) and 10% palladium on carbon (25.2 mg, 0.02 mmol) in MeOH (10 mL) was stirred under an atmosphere of hydrogen at atmospheric pressure for 3 days. The catalyst was removed by filtration and the solvent evaporated to give crude product, which was purified by flash silica chromatography, elution gradient 0 to 3% MeOH in DCM. Fractions containing the desired product were evaporated to dryness to give 6-(4-pyridin-3-ylpiperidin-1-yl)-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine (24 mg, 29%).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated
  3. customto give crude product, which
  4. customwas purified by flash silica chromatography, elution gradient 0 to 3% MeOH in DCM
  5. additionFractions containing the desired product
  6. customwere evaporated to dryness

Sources & evidence

ORD record
ord-bd3298491b474861ae88cf2f98d67169
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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