Hydrochloric Acid → HCID 67341170, compound

HRID 1674978Notes

Reaction equation

HRID 1674978 reaction equation
C([N:8]1[C@@H:13]([CH3:14])[CH2:12][N:11]([C:15]2[CH:16]=[CH:17][C:18]3[N:19]([C:21]([C:24]([F:27])([F:26])[F:25])=[N:22][N:23]=3)[N:20]=2)[C@H:10]([CH3:28])[CH2:9]1)C1C=CC=CC=1.Cl>C(O)C.[Pd]>[CH3:28][C@@H:10]1[CH2:9][NH:8][C@@H:13]([CH3:14])[CH2:12][N:11]1[C:15]1[CH:16]=[CH:17][C:18]2[N:19]([C:21]([C:24]([F:27])([F:26])[F:25])=[N:22][N:23]=2)[N:20]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59149753HCID 59149753, compound

Product 1

HCID 67341170HCID 67341170, compoundYield 30.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 6-[(2R,5S)-4-benzyl-2,5-dimethylpiperazin-1-yl]-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine (6.1 g, 15.62 mmol) in ethanol (150 mL) and 5M hydrochloric acid (9.37 mL, 46.87 mmol) was hydrogenated over 10% palladium on charcoal (1 g, 9.40 mmol) under hydrogen at 1 atmosphere for 3 days. The catalyst was filtered off and the filtrate was evaporated. The residue was taken into DCM and washed with 2M aqueous K2CO3. The organic phase was dried over MgSO4 and evaporated. The crude product was purified by MPLC silica chromatography, elution gradient 2 to 5% methanolic ammonia in DCM. Product fractions were evaporated to near dryness and crystallised from ether to afford 6-[(2R,5S)-2,5-dimethylpiperazin-1-yl]-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (1.430 g, 30.5%) as a white crystalline solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. washwashed with 2M aqueous K2CO3
  4. dry with materialThe organic phase was dried over MgSO4
  5. customevaporated
  6. customThe crude product was purified by MPLC silica chromatography, elution gradient 2 to 5% methanolic ammonia in DCM
  7. customProduct fractions were evaporated
  8. customcrystallised from ether

Sources & evidence

ORD record
ord-a89b86e21474448484944952c3b09ba7
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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