Dimethylformamide → tert-butyl 3-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)piperidine-1-carboxylate

HRID 1478592ノート

反応式

HRID 1478592 の反応式
[NH2:1][C:2]1[C:3]([NH:9][CH2:10][CH:11]2[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]2)=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.C[N:25](C=O)C>>[Br:8][C:5]1[N:4]=[C:3]2[N:9]([CH2:10][CH:11]3[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]3)[N:25]=[N:1][C:2]2=[N:7][CH:6]=1

参加物

3

反応物 2

HCID 6228DimethylformamideHCID 86626415tert-Butyl 3-((3-amino-6-bromopyrazin-2-ylamino)methyl)piperidine-1-carboxylate

生成物 1

HCID 118364769tert-butyl 3-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)piperidine-1-carboxylate収率 62%

反応条件

温度
70 °C

実験手順

tert-butyl 3-(((3-amino-6-bromopyrazine-2-yl)amino)methyl)piperidine-1-carboxylate (2.19 g, 5.70 mmol) was dissolved in DMF (15 ml), and isoamylnitrile (0.92 ml, 6.84 mmol) was slowly dropped at 0° C. After that, the mixture was stirred at 70° C. for 1 hour. After the completion of the reaction, the reaction mixture was extracted with H2O, EA, and brine, followed by drying (Na2SO4), filtration, and concentration under reduced pressure, and the residue was purified by column chromatography (EA:Hex=1:8), to give tert-butyl 3-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)piperidine-1-carboxylate (1.39 g, 62%).

後処理

  1. customAfter the completion of the reaction
  2. extractionthe reaction mixture was extracted with H2O, EA, and brine
  3. customby drying
  4. filtration(Na2SO4), filtration, and concentration under reduced pressure
  5. customthe residue was purified by column chromatography (EA:Hex=1:8)

出典と根拠

ORDレコード
ord-c5ef7cef34094ca3bd3f816f839131c7
出典データセット
uspto-grants-2016_08
特許番号
US09403831B2

反応ノート

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