Dimethylformamide → HCID 59716599, compound

HRID 2224214Notes

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+].[CH3:31][N:32]([CH:34]=[O:35])C>C(OCC)(=O)C>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C:9]2[CH:10]=[N:16][N:15]3[C:25](=[O:28])[N:12]([CH:13]([CH2:4][CH:5]([CH3:8])[CH3:6])[C:34]([NH:32][CH3:31])=[O:35])[N:11]=[C:14]3[C:8]=2[C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A solution of 7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (40 mg, 0.11 mmol), prepared as described in Example 1,2-bromo-N,4-dimethylpentanamide (25 mg) and K2CO3 (31 mg, 0.22 mmol) in DMF (2 ml), was heated at 85° C. for 1.5 hours. After this time, the reaction mixture was cooled to RT and diluted with ethyl acetate. The resultant solution was washed with water. The organic layer was dried over Na2SO4, filtered and concentrated. The crude product was purified using reverse phase preparative HPLC to give the title compound, 2-(7,8-bis(4-chlorophenyl)-3-oxo-[1,2,4]triazolo[4,3-b]pyridazin-2(3H)-yl)-N,4-dimethylpentanamide (28 mg, 40%) as a yellow solid. MS M+H=484; 1H NMR (CDCl3) δ 8.23 (1H), 7.36-7.30 (6H), 7.12 (2H), 6.90 (1H), 5.13 (1H), 2.81 (3H), 2.22 (1H), 1.98 (1H), 1.42 (1H), 0.93 (6H).

Workup

temperatureAfter this time, the reaction mixture was cooled to RT
washThe resultant solution was washed with water
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude product was purified

Sources & evidence

ORD record: ord-9cc62cd7c6d9469c9008f2f26aed4618
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07378418B2

Reaction notes

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