Potassium Hydroxide → 6-[6-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-ylsulfanyl]-5-nitro-quinoline

HRID 1890947Notes

Reaction equation

[OH-].[K+].[CH3:3][N:4]1[CH:8]=[C:7]([C:9]2[CH:10]=[CH:11][C:12]3[N:13]([C:15]([SH:18])=[N:16][N:17]=3)[N:14]=2)[CH:6]=[N:5]1.Br[C:20]1[C:21]([N+:30]([O-:32])=[O:31])=[C:22]2[C:27](=[CH:28][CH:29]=1)[N:26]=[CH:25][CH:24]=[CH:23]2>C(O)C.CO.ClCCl>[CH3:3][N:4]1[CH:8]=[C:7]([C:9]2[CH:10]=[CH:11][C:12]3[N:13]([C:15]([S:18][C:20]4[C:21]([N+:30]([O-:32])=[O:31])=[C:22]5[C:27](=[CH:28][CH:29]=4)[N:26]=[CH:25][CH:24]=[CH:23]5)=[N:16][N:17]=3)[N:14]=2)[CH:6]=[N:5]1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of KOH (146 mg, 2.6 mmol) in ethanol (10 mL) was degassed by bubbling in nitrogen for 15 min. To the solution was added 6-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-b]pyridazine-3-thiol (500 mg, 2.15 mmol) and 6-bromo-5-nitro-quinoline (600 mg, 2.36 mmol). The reaction mixture was stirred at 70° C. for 4 h, then cooled to room temperature, diluted with 10% methanol/dichloromethane and adsorbed on silica gel. Purification by flash chromatography on silica gel using a gradient of 0-7% methanol/dichloromethane afforded 659 mg of 6-[6-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-ylsulfanyl]-5-nitro-quinoline as a dark yellow solid (76% yield).

Workup

customby bubbling in nitrogen for 15 min
temperaturecooled to room temperature
customPurification by flash chromatography on silica gel using a gradient of 0-7% methanol/dichloromethane

Sources & evidence

ORD record: ord-ce39121ac46a413e8f66ab727de6db62
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507489B2

Reaction notes

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