1,1'-Carbonyldiimidazole → HCID 178461678、化合物

HRID 1019711ノート

反応式

HRID 1019711 の反応式
[Br:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[C:5]([NH2:17])=[N:4][CH:3]=1.[C:18](N1C=CN=C1)(N1C=CN=C1)=[O:19]>C1COCC1>[Br:1][C:2]1[N:7]=[C:6]2[N:8]([C@H:9]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH3:10])[C:18]([OH:19])=[N:17][C:5]2=[N:4][CH:3]=1

参加物

4

反応物 2

HCID 682631,1'-Carbonyldiimidazole2 回HCID 57880841HCID 57880841、化合物

生成物 1

HCID 178461678HCID 178461678、化合物収率 66%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (S)-6-bromo-N2-(1-phenylethyl)pyrazine-2,3-diamine (1.0 equiv) in refluxing anhydrous THF (5 volume equivalents) was added carbonyldiimidazole (CDI). Successive portions of CDI were added until the starting material was consumed (approx. 3.6 equiv total) as judged by TLC (50% EtOAc/Hexanes). After complete reaction, the mixture was cooled to room temperature and quenched by the careful addition of water until gas evolution had ceased. The mixture was diluted with 25 volume equivalents of EtOAc and washed with 3×7.5 volume equivalents of water and 1×7.5 volume equivalents of brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Flash chromatography (Biotage MPLC 5%-40% EtOAc/Hexanes) provided the title compound (66%) as a white solid. LCMS m/z (APCI)=319.0, 321.0 (M+H).

後処理

  1. customwas consumed (approx. 3.6 equiv total)
  2. customAfter complete reaction
  3. customquenched by the careful addition of water until gas evolution
  4. additionThe mixture was diluted with 25 volume equivalents of EtOAc
  5. washwashed with 3×7.5 volume equivalents of water and 1×7.5 volume equivalents of brine
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-79192aad17b6460ba4bec03bff280adc
出典データセット
uspto-grants-2014_05
特許番号
US08716291B2

反応ノート

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