Potassium Carbonate → HCID 59716676, compound

HRID 1160219Notes

Reaction equation

[Cl:1][C:2]1[C:3]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:5]2[N:6]([C:8](=[O:11])[NH:9][N:10]=2)[N:7]=1.C([O-])([O-])=O.[K+].[K+].[F:32][C:33]([F:43])([F:42])[C:34]1[CH:41]=[CH:40][C:37]([CH2:38]Br)=[CH:36][CH:35]=1>CN(C=O)C.O>[F:32][C:33]([F:42])([F:43])[C:34]1[CH:41]=[CH:40][C:37]([CH2:38][N:9]2[C:8](=[O:11])[N:6]3[N:7]=[C:2]([Cl:1])[C:3]([C:19]4[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=4)=[C:4]([C:12]4[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=4)[C:5]3=[N:10]2)=[CH:36][CH:35]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of 6-chloro-7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (750 mg, 1.92 mmol), prepared as described in Example 1F, in DMF (10 mL) was added K2CO3 (270 mg, 1.95 mmol) and 4-(trifluoromethyl)benzyl bromide (460 mg, 1.92 mmol). The reaction mixture was stirred at 75° C. for 1 h under Argon. It was cooled to RT diluted with water (50 mL) and the solid was collected by filtration. The solid was washed with water (25 mL×2) and dried in a vacuum oven at 50° C. overnight to give the title compound, 2-(4-(trifluoromethyl)benzyl)-6-chloro-7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (990 mg, 94%) as yellow powder. HPLC: 4.23 min; MS: M+H=549.

Workup

temperatureIt was cooled to RT
filtrationthe solid was collected by filtration
washThe solid was washed with water (25 mL×2)
customdried in a vacuum oven at 50° C. overnight

Sources & evidence

ORD record: ord-8d5f6c4eb1484da18a0cd51f0d063319
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816357B2

Reaction notes

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