1,1'-Carbonyldiimidazole → HCID 178446212, 화합물

HRID 2262675노트

반응식

HRID 2262675 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[C:5]([NH2:8])=[N:6][CH:7]=1.C1N=CN([C:20](N2C=NC=C2)=[O:21])C=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[N:9]([CH:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[C:20]([OH:21])=[N:8][C:5]2=[N:6][CH:7]=1

참가 물질

4

반응물 2

HCID 682631,1'-Carbonyldiimidazole2회HCID 59594561HCID 59594561, 화합물

생성물 1

HCID 178446212HCID 178446212, 화합물수율 71%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a refluxing solution of 5-chloro-N3-(pentan-3-yl)pyridine-2,3-diamine (1.5 g, 7.0 mmol, 1.0 equiv) in THF (10 mL) was added CDI portionwise until starting material was consumed as judged by TLC (50% EtOAC/Hexanes; UV). Approximately 10 equiv of carbonyldiimidazole were required. The resulting reaction mixture was cooled to room temperature, and the excess carbonyldiimidazole was quenched by the careful addition of water. The mixture was diluted with EtOAc, and the layers were separated. The organic layer was washed with satd. aq. NaHCO3 twice, and brine once. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Purification by silica gel MPLC provided 6-chloro-1-(pentan-3-yl)-1H-imidazo[4,5-b]pyridin-2-ol as a white solid (1.2 g, 71%). m/z=240.1 [M+H]+

후처리

  1. customwas consumed
  2. customThe resulting reaction mixture
  3. customthe excess carbonyldiimidazole was quenched by the careful addition of water
  4. additionThe mixture was diluted with EtOAc
  5. customthe layers were separated
  6. washThe organic layer was washed with satd
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification by silica gel MPLC

출처 및 근거

ORD 기록
ord-373d3db87d304edc97d935269ad0961e
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07851484B2

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