4-amino-N-methylbenzene-1-sulfonamide → 4-(3-bromo-6-chloroimidazo[1,2-b]pyridazin-8-ylamino)-N-methylbenzenesulfonamide

HRID 2239906Notes

Reaction equation

[Br:1][C:2]1[N:6]2[N:7]=[C:8]([Cl:12])[CH:9]=[C:10](Br)[C:5]2=[N:4][CH:3]=1.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([NH:23][CH3:24])(=[O:22])=[O:21])=[CH:16][CH:15]=1.CC(C)([O-])C.[K+]>C1COCC1>[Br:1][C:2]1[N:6]2[N:7]=[C:8]([Cl:12])[CH:9]=[C:10]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([S:20]([NH:23][CH3:24])(=[O:22])=[O:21])=[CH:16][CH:15]=3)[C:5]2=[N:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

In a 100 ml round bottom flask was added 3,8-dibromo-6-chloroimidazo[1,2-b]pyridazine (0.122 g, 0.391 mmol) from Example XXIV, step (1a), 4-amino-N-methylbenzenesulfonamide (0.080 g, 0.430 mmol), and THF (3.9 ml, 0.1 M). Potassium tert-butoxide (0.976 mL, 0.976 mmol) was added drop-wise and the reaction was stirred at 25° C. overnight. The mixture was concentrated and diluted with ethyl acetate and water. The layers were separated and the organic was washed water (20 ml), then brine (10 ml), dried over Na2SO4, filtered and concentrated to provide 4-(3-bromo-6-chloroimidazo[1,2-b]pyridazin-8-ylamino)-N-methylbenzenesulfonamide (0.090 g, 55.3% yield) as a brownish solid. m/z=(417, M+1).

Workup

concentrationThe mixture was concentrated
additiondiluted with ethyl acetate and water
customThe layers were separated
washthe organic was washed water (20 ml)
dry with materialbrine (10 ml), dried over Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-b65bd2ea9b3646b7825958745e902b29
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723336B2

Reaction notes

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