Cesium fluoride → 3-Bromo-N-[(1S)-1-(5-fluoropyrimidin-2-yl)ethyl]imidazo[1,2-b]pyridazin-6-amine

HRID 2279072노트

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HRID 2279072 반응식
[Br:1][C:2]1[N:6]2[N:7]=[C:8](Cl)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[F:12][C:13]1[CH:14]=[N:15][C:16]([C@@H:19]([NH2:21])[CH3:20])=[N:17][CH:18]=1.[F-].[Cs+]>CS(C)=O>[Br:1][C:2]1[N:6]2[N:7]=[C:8]([NH:21][C@H:19]([C:16]3[N:17]=[CH:18][C:13]([F:12])=[CH:14][N:15]=3)[CH3:20])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1

참가 물질

5

반응물 3

HCID 25953Cesium fluorideHCID 128723233-Bromo-6-chloroimidazo(1,2-b)pyridazineHCID 55285341(S)-1-(5-Fluoropyrimidin-2-YL)ethanamine

생성물 1

HCID 867023283-Bromo-N-[(1S)-1-(5-fluoropyrimidin-2-yl)ethyl]imidazo[1,2-b]pyridazin-6-amine수율 64%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
180 °C

실험 절차

A mixture of 3-bromo-6-chloroimidazo[1,2-b]pyridazine (Preparation 1b, 0.2 g, 0.86 mmol), (1S)-1-(5-fluoropyrimidin-2-yl)ethanamine (prepared according to the method described in WO2006/82392A1, 0.24 g, 1.72 mmol), cesium fluoride (1.31 g, 8.60 mmol) and dimethylsulfoxide (5 mL) was heated at 180° C. for 2 hours in a sealed tube. The reaction was cooled down, filtered through Celite® eluting with ethyl acetate and the filtrate was washed with water, dried over magnesium sulphate and the solvent removed under reduced pressure. The residue was purified by flash chromatography (40-70% acetone in hexanes) to give the title compound (0.11 g, 64%) as a brown foam.

후처리

  1. customprepared
  2. temperatureThe reaction was cooled down
  3. filtrationfiltered through Celite®
  4. washeluting with ethyl acetate
  5. washthe filtrate was washed with water
  6. dry with materialdried over magnesium sulphate
  7. customthe solvent removed under reduced pressure
  8. customThe residue was purified by flash chromatography (40-70% acetone in hexanes)

출처 및 근거

ORD 기록
ord-928e98ec59834057bfd4880bf1bfd7e5
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133200B2

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