Sodium Hydroxide → HCID 21187496, compound

HRID 1383831Notes

Reaction equation

HRID 1383831 reaction equation
Cl[C:2]1[C:3]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:9][N:10]=2)[N:7]=1.[OH-:23].[Na+]>O1CCOCC1.O>[C:11]1([C:8]2[N:6]3[NH:7][C:2](=[O:23])[C:3]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:4][C:5]3=[N:10][N:9]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11392626HCID 11392626, compound

Product 1

HCID 21187496HCID 21187496, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 6-chloro-3,7-diphenyl-1,2,4-triazolo[4,3-b]pyridazine (from Example 2, Step c) (1.02 g, 3.34 mmol) in 1,4-dioxane (60 ml) and water (12 ml) was added 4 M aqueous NaOH (4.17 ml, 16.7 mmol), and the solution was heated at reflux for 7.5 h whilst stirring magnetically. The mixture was then concentrated in vacuo and the aqueous residue was partitioned between water (200 ml) and diethyl ether (100 ml). The aqueous layer was then acidified with 5 M aqueous HCl until the pH was ca. 3. The resulting precipitated solid was collected by filtration, washed with water, then hexane, and dried at 60° C. under vacuum to give 0.8885 g (92%) of the title compound as a white solid. 1H NMR (360 MHz, d6-DMSO) δ 7.47-7.63 (6H, m), 7.71 (2H, dd, J=8.0, J=1.8 Hz), 8.31 (1H, s), 8.46 (2H, m), 12.80 (1H, br s); MS (ES+) m/e 289 [MH]+.

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 7.5 h
  3. concentrationThe mixture was then concentrated in vacuo
  4. customthe aqueous residue was partitioned between water (200 ml) and diethyl ether (100 ml)
  5. customThe resulting precipitated solid
  6. filtrationwas collected by filtration
  7. washwashed with water
  8. dry with materialhexane, and dried at 60° C. under vacuum

Sources & evidence

ORD record
ord-a271e100a1374e2b883284852c08c099
Source dataset
uspto-grants-2001_07
Patent number
US06255305B1

Reaction notes

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