Aminopyridazine → (1-Imidazo[1,2-b]pyridazin-2-yl-ethyl)-carbamic acid benzyl ester

HRID 2036655ノート

反応式

HRID 2036655 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[N:2]=1.[CH2:8]([O:15][C:16](=[O:24])[NH:17][CH:18]([CH3:23])[C:19](=O)[CH2:20]Br)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CCO>[CH2:8]([O:15][C:16](=[O:24])[NH:17][CH:18]([C:19]1[N:7]=[C:3]2[CH:4]=[CH:5][CH:6]=[N:1][N:2]2[CH:20]=1)[CH3:23])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

4

反応物 2

HCID 230373AminopyridazineHCID 73196234Benzyl (4-bromo-3-oxobutan-2-yl)carbamate

生成物 1

HCID 67433032(1-Imidazo[1,2-b]pyridazin-2-yl-ethyl)-carbamic acid benzyl ester

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of pyridazin-3-ylamine (2 g, 21.05 mmol) and (3-bromo-1-methyl-2-oxopropyl)-carbamic acid benzyl ester (7.5 g, 25.26 mmol) in EtOH (25 mL) was heated to reflux overnight. After completion, the reaction mixture was cooled to rt. EtOH was removed in vacuo. The residue was dissolved in EtOAc. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography using silica gel (100-200 mesh) and 0-5% MeOH in DCM to provide (1-imidazo[1,2-b]pyridazin-2-yl-ethyl)-carbamic acid benzyl ester: LC-MS (ESI) m/z 297.3 [M+H]+.

後処理

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customEtOH was removed in vacuo
  4. dissolutionThe residue was dissolved in EtOAc
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by column chromatography

出典と根拠

ORDレコード
ord-39e76ec047ac4006adff339bc5247f70
出典データセット
uspto-grants-2013_11
特許番号
US08575183B2

反応ノート

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