Dimethylformamide → HCID 59716679, compound

HRID 2224216Notes

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)[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:25]([O-:28])([O-])=O.[K+].[K+].CN([CH:34]=[O:35])C>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:35][CH2:34][CH2:14][N:15]2[C:25](=[O:28])[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:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

The solution of 7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (30 mg, 0.084 mmol), prepared as described in Example 1,1-(2-bromoethoxy)-4-chlorobenzene (22 mg, 0.094 mmol) and K2CO3 (18 mg, 0.013 mmol) in DMF (1 ml) was heated at 70° C. for 4 hours. After this time, the solution was cool to RT and diluted with ethyl acetate. The resultant solution was then washed with water. The organic layer was dried over Na2SO4, filtered and concentrated. The crude material was purified by preparative HPLC to give the title compound, 2-(2-(4-chlorophenoxy)ethyl)-7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (25.5 mg, 59%) was obtained as a yellow solid. MS M+H=511; 1H NMR (CDCl3) δ 8.19 (1H), 7.34 (4H), 7.28 (2H), 7.18 (2H), 7.28 (2H), 6.80 (2H), 4.44 (2H), 4.36 (2H).

Workup

temperatureAfter this time, the solution was cool to RT
washThe resultant solution was then washed with water
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude material was purified by preparative HPLC

Sources & evidence

ORD record: ord-ffa4c377e6504cbd9559bddee936059c
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07378418B2

Reaction notes

Loading…