Sodium Hydroxide → HCID 178433944, compound

HRID 985440Notes

Reaction equation

HRID 985440 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]2[N:14]=[C:15]([O:17]S(C3C=CC(C)=CC=3)(=O)=O)[CH:16]=[C:12]2[C:11]([CH3:28])=[N:10][N:9]=1.[OH-].[Na+]>O1CCOCC1.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]2[N:14]=[C:15]([OH:17])[CH:16]=[C:12]2[C:11]([CH3:28])=[N:10][N:9]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 87418381Toluene-4-sulfonic acid 7-(2-fluorophenyl)-4-methylpyrazolo[1,5-d][1,2,4]triazin-2-yl ester

Product 1

HCID 178433944HCID 178433944, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of toluene-4-sulfonic acid 7-(2-fluorophenyl)-4-methylpyrazolo[1,5-d][1,2,4]triazin-2-yl ester (3.39 g, 8.51 mmol) in 1,4-dioxane (150 ml) and water (30 ml) was added 4 N aqueous NaOH (10.64 ml, 42.6 mmol) and the mixture was stirred at room temperature for 4 h. The mixture was concentrated in vacuo to about 30 ml, and the aqueous residue was diluted with water (150 ml) and washed with ethyl acetate (50 ml). The remaining aqueous layer was acidified to pH 5 with 5 N aqueous HCl (4 ml) and the resulting precipitate was collected by filtration, washed with water and dried at 60° C. under vacuum to leave 1.98 g (95%) of the title compound as a cream solid: 1H NMR (360 MHz, DMSO-d6) δ 2.68 (3H, s), 6.38 (1H, s), 7.41-7.47 (2H, m), 7.66-7.77 (2H, m); MS (ES+) m/e 245 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated in vacuo to about 30 ml
  2. additionthe aqueous residue was diluted with water (150 ml)
  3. washwashed with ethyl acetate (50 ml)
  4. filtrationthe resulting precipitate was collected by filtration
  5. washwashed with water
  6. customdried at 60° C. under vacuum

Sources & evidence

ORD record
ord-9a2fc35adb554ba8ab25bcde0e50afa2
Source dataset
uspto-grants-2005_03
Patent number
US06872720B2

Reaction notes

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