Lithium hydroxide, monohydrate → HCID 67340981, compound

HRID 1675137Notes

Reaction equation

HRID 1675137 reaction equation
O.[OH-].[Li+].[F:4][C:5]([F:33])([F:32])[C:6]1[N:10]2[N:11]=[C:12]([N:15]3[CH2:20][CH2:19][N:18]([C:21]4[CH:31]=[CH:30][C:24]([C:25]([O:27]CC)=[O:26])=[CH:23][CH:22]=4)[CH2:17][CH2:16]3)[CH:13]=[CH:14][C:9]2=[N:8][N:7]=1>CO.O>[F:33][C:5]([F:4])([F:32])[C:6]1[N:10]2[N:11]=[C:12]([N:15]3[CH2:16][CH2:17][N:18]([C:21]4[CH:31]=[CH:30][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=4)[CH2:19][CH2:20]3)[CH:13]=[CH:14][C:9]2=[N:8][N:7]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrate2×HCID 67341147HCID 67341147, compound

Product 1

HCID 67340981HCID 67340981, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Lithium hydroxide monohydrate (0.373 g, 8.90 mmol) was added to ethyl 4-[4-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperazin-1-yl]benzoate (3.40 g, 8.09 mmol) in a mixture of MeOH (60 mL) and water (30 mL). The resulting suspension was stirred at 50° C. for 16 hours. Further lithium hydroxide monohydrate (0.373 g, 8.90 mmol) was added, the temperature was increased to 65° C. and the suspension was stirred for a further 6 hours. The reaction mixture was cooled to room temperature and the MeOH evaporated. The residues were dissolved in water (200 mL) and filtered. The filtrate was acidified with 1M citric acid until precipitation ceased, and the precipitate was collected by filtration, washed with water and dried under vacuum to afford 4-[4-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperazin-1-yl]benzoic acid (3.17 g, 100%) as a solid.

Workup

  1. temperaturethe temperature was increased to 65° C.
  2. stirringthe suspension was stirred for a further 6 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customthe MeOH evaporated
  5. dissolutionThe residues were dissolved in water (200 mL)
  6. filtrationfiltered
  7. customThe filtrate was acidified with 1M citric acid until precipitation
  8. filtrationthe precipitate was collected by filtration
  9. washwashed with water
  10. customdried under vacuum

Sources & evidence

ORD record
ord-30e4063aad47419f864721edf9887133
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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