Sodium Hydroxide → HCID 178515394, compound

HRID 1016397Notes

Reaction equation

HRID 1016397 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[CH:11]=[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[CH:11]=[N:10][N:9]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 87798670Toluene-4-sulfonic Acid 7-(2-Fluorophenyl)pyrazolo[1,5-d][1,2,4]triazin-2-yl Ester

Product 1

HCID 178515394HCID 178515394, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of toluene-4-sulfonic acid 7-(2-fluorophenyl)pyrazolo[1,5-d][1,2,4]triazin-2-yl ester (82.0 mg, 0.213 mmol) in 1,4-dioxane (4 ml) and water (0.8 ml) was added aqueous 4 N NaOH solution (0.270 ml, 1.08 mmol). The solution was heated at 60° C. for 3 h, then the solvents were removed in vacuo. The residue was dissolved in water (10 ml) and washed with ethyl acetate (10 ml). The aqueous layer was acidified to pH<3 and extracted with dichloromethane (6×25 ml). The combined organic extracts were dried (Na2SO4) and evaporated in vacuo to leave 40.7 mg (83%) of the title compound; 1H NMR (360 MHz, d6-DMSO) δ 6.34 (1H, s), 7.42-7.48 (2H, m), 7.71 (1H, m), 7.79 (1H, td, J 7.2 and 1.7 Hz), 9.40 (1H, s), 11.74 (1H, s).

Workup

  1. customthe solvents were removed in vacuo
  2. dissolutionThe residue was dissolved in water (10 ml)
  3. washwashed with ethyl acetate (10 ml)
  4. extractionextracted with dichloromethane (6×25 ml)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-d9dba32cd17142ef9b9653f66da2609e
Source dataset
uspto-grants-2002_11
Patent number
US06476030B1

Reaction notes

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