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

HRID 539006노트

반응식

HRID 539006 반응식
[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]

참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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]+.

후처리

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

출처 및 근거

ORD 기록
ord-d1641a266f3a4f98bb0a19edabfa3b6b
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865726B2

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