Phenol → 4-(Trifluoromethyl)benzyl-7-(4-chloro-phenyl)-8-phenoxy-2H-[1,2,4]triazolo[4,3-b]pyridazin-3-one

HRID 2224275Notes

Reaction equation

HRID 2224275 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:27]=[CH:26][C:6]([CH2:7][N:8]2[C:24](=[O:25])[N:11]3[N:12]=[CH:13][C:14]([C:17]4[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=4)=[C:15](Cl)[C:10]3=[N:9]2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[C:36]1([OH:42])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>CN(C=O)C.[OH-].[Na+]>[F:29][C:2]([F:1])([F:28])[C:3]1[CH:27]=[CH:26][C:6]([CH2:7][N:8]2[C:24](=[O:25])[N:11]3[N:12]=[CH:13][C:14]([C:17]4[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=4)=[C:15]([O:42][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:10]3=[N:9]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 597166974-(Trifluoromethyl)benzyl-8-chloro-7-(4-chlorophenyl)-2H-[1,2,4]triazolo[4,3-b]pyridazin-3-one

Product 1

HCID 597168494-(Trifluoromethyl)benzyl-7-(4-chloro-phenyl)-8-phenoxy-2H-[1,2,4]triazolo[4,3-b]pyridazin-3-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 2-(4-(trifluoromethyl)benzyl-8-chloro-7-(4-chlorophenyl)-2H-[1,2,4]triazolo[4,3-b]pyridazin-3-one (16.5 mg, 0.376 mmol) prepared as described in Example 359, in 0.3 mL of DMF at RT, potassium carbonate (19.4 mg, 0.14 mmol) was added followed by phenol (13.2 mg, 0.14 mmol). The mixture was stirred for 4 h. After this time, the reaction mixture was diluted with 5 mL of 1N aqueous sodium hydroxide. The precipitate was collected by filtration and washed with 1N aqueous NaOH, and water. The solid was dried to the title compound, 2-(4-(trifluoromethyl)benzyl-7-(4-chlorophenyl)-8-phenoxy-2H-[1,2,4]triazolo[4,3-b]pyridazin-3-one (15.8 mg) as light yellow solid. HPLC RT: 4.02 min; MS, M+H=497; 1H NMR (CDCl3): δ 8.21 (s, 1H), 7.52-6.97 (m, 13H), 5.12 (s, 2H).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with 1N aqueous NaOH, and water
  3. dry with materialThe solid was dried to the title compound

Sources & evidence

ORD record
ord-cb7c2eebb9af422ea148b10a2c6ca92e
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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