1,1'-Carbonyldiimidazole → HCID 178446212、化合物

HRID 2262675ノート

反応式

HRID 2262675 の反応式
[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

参加物

4

反応物 2

HCID 682631,1'-Carbonyldiimidazole2 回HCID 59594561HCID 59594561、化合物

生成物 1

HCID 178446212HCID 178446212、化合物収率 71%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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]+

後処理

  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

出典と根拠

ORDレコード
ord-373d3db87d304edc97d935269ad0961e
出典データセット
uspto-grants-2010_12
特許番号
US07851484B2

反応ノート

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