Triethylamine → (S)-4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzohydrazide

HRID 538999Notes

Reaction equation

HRID 538999 reaction equation
CCN=C=NCCCN(C)C.[CH:12]([C@H:15]1[CH2:19][O:18][C:17](=[O:20])[N:16]1[C:21]1[CH:26]=[CH:25][N:24]2[N:27]=[CH:28][C:29]([C:30]3[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][CH:31]=3)=[C:23]2[N:22]=1)([CH3:14])[CH3:13].C1C=CC2N(O)[N:46]=[N:45]C=2C=1.O.O.NN.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[CH:12]([C@H:15]1[CH2:19][O:18][C:17](=[O:20])[N:16]1[C:21]1[CH:26]=[CH:25][N:24]2[N:27]=[CH:28][C:29]([C:30]3[CH:31]=[CH:32][C:33]([C:34]([NH:45][NH2:46])=[O:35])=[CH:37][CH:38]=3)=[C:23]2[N:22]=1)([CH3:14])[CH3:13]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 24654Hydrazine hydrate (1:1)HCID 27960291-Hydroxybenzotriazole hydrateHCID 67034480(S)-4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzoic acid

Product 1

HCID 67033928(S)-4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzohydrazideYield 64%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

EDCI (2.39 g, 12.45 mmol) was added to a mixture of (S)-4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzoic acid (0.76 g, 2.1 mmol) and HOBT-H2O (0.95 g, 6.226 mmol) in DMF (10 mL) at ambient temperature, and the reaction mixture was stirred for 20 minutes at ambient temperature. A solution of hydrazine hydrate (0.31 mL, 6.2 mmol) in DMF and triethylamine (1.5 mL, 10.38 mmol) were added. The resulting mixture was stirred for 1 hour at ambient temperature. The reaction mixture was diluted with EtOAc, washed with aqueous NH4Cl, NaHCO3, and brine, dried over MgSO4, and concentrated under reduced pressure. The crude was purified by silica gel flash column chromatography (0-5% MeOH in dichloromethane) to afford 0.50 g (64%) of (S)-4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzohydrazide. LCMS (APCI+) m/z 381.4 [M+H]+.

Workup

  1. stirringThe resulting mixture was stirred for 1 hour at ambient temperature
  2. washwashed with aqueous NH4Cl, NaHCO3, and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude was purified by silica gel flash column chromatography (0-5% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-6d6bb08b0f9c40dda515d2373c84fd0e
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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