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

HRID 2239906

반응식

HRID 2239906 반응식
[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

참가 물질

5

반응물 3

HCID 743684-amino-N-methylbenzene-1-sulfonamideHCID 23665647Potassium tert-butoxideHCID 446307233,8-Dibromo-6-chloroimidazo[1,2-b]pyridazine

생성물 1

HCID 866185264-(3-bromo-6-chloroimidazo[1,2-b]pyridazin-8-ylamino)-N-methylbenzenesulfonamide수율 55.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
25 °C

실험 절차

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).

후처리

  1. concentrationThe mixture was concentrated
  2. additiondiluted with ethyl acetate and water
  3. customThe layers were separated
  4. washthe organic was washed water (20 ml)
  5. dry with materialbrine (10 ml), dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b65bd2ea9b3646b7825958745e902b29
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723336B2

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