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

HRID 539006Notes

Reaction equation

HRID 539006 reaction equation
[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]

Participants

4

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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]+.

Workup

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

Sources & evidence

ORD record
ord-d1641a266f3a4f98bb0a19edabfa3b6b
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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