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

HRID 2279072ノート

反応式

HRID 2279072 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
180 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-928e98ec59834057bfd4880bf1bfd7e5
出典データセット
uspto-grants-2015_09
特許番号
US09133200B2

反応ノート

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