Lithium hydroxide, monohydrate → 4-[[1-[3-(Trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]oxy]benzoic acid

HRID 1675055Notes

Reaction equation

O.[OH-].[Li+].[F:4][C:5]([F:34])([F:33])[C:6]1[N:10]2[N:11]=[C:12]([N:15]3[CH2:20][CH2:19][CH:18]([O:21][C:22]4[CH:32]=[CH:31][C:25]([C:26]([O:28]CC)=[O:27])=[CH:24][CH:23]=4)[CH2:17][CH2:16]3)[CH:13]=[CH:14][C:9]2=[N:8][N:7]=1>CO.O>[F:34][C:5]([F:4])([F:33])[C:6]1[N:10]2[N:11]=[C:12]([N:15]3[CH2:16][CH2:17][CH:18]([O:21][C:22]4[CH:32]=[CH:31][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=4)[CH2:19][CH2:20]3)[CH:13]=[CH:14][C:9]2=[N:8][N:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Lithium hydroxide monohydrate (0.488 g, 20.40 mmol) was added to ethyl 4-[[1-[3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]oxy]benzoate (2.22 g, 5.10 mmol) in MeOH (80 mL) and water (40.0 mL). The resulting suspension was stirred at 50° C. for 2 days. The reaction was cooled to room temperature, the methanol was evaporated and the aqueous residues treated with citric acid until precipitation ceased. The precipitate was collected by filtration, washed with water and dried to afford 4-[[1-[3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]oxy]benzoic acid (2.020 g, 97%) as a solid.

Workup

temperatureThe reaction was cooled to room temperature
customthe methanol was evaporated
additionthe aqueous residues treated with citric acid until precipitation
filtrationThe precipitate was collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-e65e39f7d2a240499f8a1ce909a675ef
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003649B2

Reaction notes

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