Potassium Carbonate → HCID 59716884, compound

HRID 2224232Notes

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.[O:25]1[CH:28]([CH3:29])[C:26]1([CH3:30])[CH3:27].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[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])[N:15]([CH:28]([C:26]([OH:25])([CH3:30])[CH3:27])[CH3:29])[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

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (300 mg, 0.84 mmol), prepared as described in Example 1, in 0.6 mL of DMF was added 2,3-epoxy-2-methylbutane (4.8 mg, 0.056 mmol), followed by K2CO3 (15.5 mg, 0.112 mmol). The mixture was heated at 85° C. for 16 h. After this time, an additional 10 mg of K2CO3 and 2,3-epoxy-2-methylbutane (4.8 mg, 0.056 mmol) were added. The reaction was allowed to continue stirring at 85° C. for an additional 48 h. The reaction was cooled to RT and filtered. The collected solution was concentrated under reduced pressure. The residue was purified by reverse phase HPLC to give the title compound, 7,8-bis(4-chlorophenyl)-2-(3-hydroxy-3-methylbutan-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (5 mg, 20% yield) as a yellow oil. MS [M+H]+: found 443; 1H NMR (CDCl3, 400 MHz) δ 8.25 (s, 1H), 7.39-7.27 (m, 6H), 7.14 (dd, 2H), 4.55 (q, 1H), 1.52 (d, 3H), 1.34 (s, 1H), 1.23 (s, 1H).

Workup

temperatureThe reaction was cooled to RT
filtrationfiltered
concentrationThe collected solution was concentrated under reduced pressure
customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record: ord-fc919afacfb44c92bfc23bf4a54897c0
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07378418B2

Reaction notes

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