1,1'-Carbonyldiimidazole → HCID 178461678, 화합물

HRID 1019711노트

반응식

HRID 1019711 반응식
[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

참가 물질

4

반응물 2

HCID 682631,1'-Carbonyldiimidazole2회HCID 57880841HCID 57880841, 화합물

생성물 1

HCID 178461678HCID 178461678, 화합물수율 66%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-79192aad17b6460ba4bec03bff280adc
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716291B2

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