Water → HCID 11988882, compound

HRID 2224202Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[N:12][N:11]3[C:14](=[O:17])[NH:15][N:16]=[C:10]3[C:9]=2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Cl:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36]Br)=[CH:34][CH:33]=1.O>CN(C=O)C>[Cl:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36][N:15]2[C:14](=[O:17])[N:11]3[N:12]=[CH:13][C:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=4)=[C:9]([C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=4)[C:10]3=[N:16]2)=[CH:34][CH:33]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (0.4 g, 1.1 mmol), prepared as described in Example 1 in DMF (5 mL) was added K2CO3 (0.46 g, 3.3 mmol) and 4-chlorobenzyl bromide (0.28 g, 1.3 mmol). The reaction mixture was heated at 60° C. for 20 min. After this time, water (50 mL) was added to the reaction mixture and the resultant solid was collected by filtration. The final product (0.32 g, 60%) was obtained by purification using reverse phase preparative HPLC. MS (M+H)=481; 1H NMR (CDCl3): δ 8.18 (1H, s), 7.25-7.40 (10H, m), 7.08 (2H, d, J=10.0 Hz), 5.18 (2H, s).

Workup

filtrationthe resultant solid was collected by filtration

Sources & evidence

ORD record: ord-80bcf39e6083495bbc8a93818d3a86ea
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07378418B2

Reaction notes

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