Ethanolamine → (S)-N-(2-hydroxyethyl)-2-(4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzoyl)hydrazinecarboxamide

HRID 539006ノート

反応式

HRID 539006 の反応式
[CH:1]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[C:10]1[CH:15]=[CH:14][N:13]2[N:16]=[CH:17][C:18]([C:19]3[CH:24]=[CH:23][C:22]([C:25]4[O:29][C:28](=[O:30])[NH:27][N:26]=4)=[CH:21][CH:20]=3)=[C:12]2[N:11]=1)([CH3:3])[CH3:2].[NH2:31][CH2:32][CH2:33][OH:34]>CCO>[OH:34][CH2:33][CH2:32][NH:31][C:28]([NH:27][NH:26][C:25](=[O:29])[C:22]1[CH:21]=[CH:20][C:19]([C:18]2[CH:17]=[N:16][N:13]3[CH:14]=[CH:15][C:10]([N:5]4[C@@H:4]([CH:1]([CH3:2])[CH3:3])[CH2:8][O:7][C:6]4=[O:9])=[N:11][C:12]=23)=[CH:24][CH:23]=1)=[O:30]

参加物

4

反応物 2

HCID 700EthanolamineHCID 67034488(S)-5-(4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)phenyl)-1,3,4-oxadiazol-2(3H)-one

生成物 1

HCID 67033962(S)-N-(2-hydroxyethyl)-2-(4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzoyl)hydrazinecarboxamide収率 29.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A suspension of (S)-5-(4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)phenyl)-1,3,4-oxadiazol-2(3H)-one (42.8 mg, 0.105 mmol) and 2-aminoethanol (19.1 μL, 0.316 mmol) in EtOH (2 mL) was heated to reflux for 22 hours. After the reaction mixture was cooled to ambient temperature, the solvent was removed under reduced pressure. The crude product was flash chromatographed (0-10% MeOH in dichloromethane) to afford 14.4 mg (29%) of (S)—N-(2-hydroxyethyl)-2-(4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzoyl)hydrazinecarboxamide. LCMS (APCI−) m/z 466.5 [M−H]+.

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 22 hours
  3. customthe solvent was removed under reduced pressure
  4. customchromatographed (0-10% MeOH in dichloromethane)

出典と根拠

ORDレコード
ord-d1641a266f3a4f98bb0a19edabfa3b6b
出典データセット
uspto-grants-2014_10
特許番号
US08865726B2

反応ノート

読み込み中…