Sodium Hydroxide → HCID 67339697, compound

HRID 1675080Notes

Reaction equation

HRID 1675080 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[N:7]2[N:8]=[C:9]([N:12]3[CH2:17][CH2:16][CH:15]([C:18]4[C:26]5[C:21](=[CH:22][CH:23]=[C:24]([C:27]([O:29]C)=[O:28])[CH:25]=5)[NH:20][CH:19]=4)[CH2:14][CH2:13]3)[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1.[OH-].[Na+]>CO>[F:32][C:2]([F:1])([F:31])[C:3]1[N:7]2[N:8]=[C:9]([N:12]3[CH2:17][CH2:16][CH:15]([C:18]4[C:26]5[C:21](=[CH:22][CH:23]=[C:24]([C:27]([OH:29])=[O:28])[CH:25]=5)[NH:20][CH:19]=4)[CH2:14][CH2:13]3)[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67340259HCID 67340259, compound

Product 1

HCID 67339697HCID 67339697, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-[1-[3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]-1H-indole-5-carboxylate (3.28 g, 7.38 mmol) and 2M NaOH (10 mL, 7.38 mmol) in methanol (80 mL) were heated under reflux for 40 hours. The resulting solution was concentrated by evaporation, then acidified to pH 2-3 with 2M hydrochloric acid to give a colourless precipitate. The precipitate was collected by filtration, washed sequentially with water, acetonitrile and ether and dried under vacuum to afford 3-[1-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]-1H-indole-5-carboxylic acid (2.83 g, 89%) as a colourless solid.

Workup

  1. temperatureunder reflux for 40 hours
  2. concentrationThe resulting solution was concentrated by evaporation
  3. customto give a colourless precipitate
  4. filtrationThe precipitate was collected by filtration
  5. washwashed sequentially with water, acetonitrile and ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-16be4d9ad7c24fcd9b3128553ba51960
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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