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

HRID 539075Notes

Reaction equation

HRID 539075 reaction equation
C(N=C=NCCCN(C)C)C.[F:12][C:13]1[CH:18]=[CH:17][C:16]([C@H:19]2[CH2:23][O:22][C:21](=[O:24])[N:20]2[C:25]2[CH:30]=[CH:29][N:28]3[N:31]=[CH:32][C:33]([C:34]4[CH:42]=[CH:41][C:37]([C:38]([OH:40])=O)=[CH:36][CH:35]=4)=[C:27]3[N:26]=2)=[CH:15][CH:14]=1.OC1C2N=[N:50][NH:49]C=2C=CC=1.O.NN.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[F:12][C:13]1[CH:18]=[CH:17][C:16]([C@H:19]2[CH2:23][O:22][C:21](=[O:24])[N:20]2[C:25]2[CH:30]=[CH:29][N:28]3[N:31]=[CH:32][C:33]([C:34]4[CH:42]=[CH:41][C:37]([C:38]([NH:49][NH2:50])=[O:40])=[CH:36][CH:35]=4)=[C:27]3[N:26]=2)=[CH:15][CH:14]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 24654Hydrazine hydrate (1:1)HCID 67034785(S)-4-(5-(4-(4-fluorophenyl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 67035490(S)-4-(5-(4-(4-fluorophenyl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzohydrazideYield 79%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide (0.1031 g, 0.5378 mmol) was added to a mixture of (S)-4-(5-(4-(4-fluorophenyl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzoic acid (0.075 g, 0.1793 mmol) and hydroxybenzotriazole (0.073 g, 0.5378 mmol) in DMF (0.6 mL) at ambient temperature. After stirring for 10 minutes, hydrazine monohydrate (0.02609 mL, 0.5378 mmol), followed by triethylamine (0.07496 mL, 0.5378 mmol) were added. The mixture was stirred at ambient temperature for 4 hours, diluted with EtOAc, washed with aqueous saturated NH4Cl, brine, dried (phase separator silicone treated filter paper), concentrated and purified on silica gel (2-8% MeOH in DCM) to provide (S)-4-(5-(4-(4-fluorophenyl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzohydrazide (0.061 g, 79% yield) as a clear oil.

Workup

  1. additionwere added
  2. stirringThe mixture was stirred at ambient temperature for 4 hours
  3. washwashed with aqueous saturated NH4Cl, brine
  4. customdried
  5. addition(phase separator silicone treated filter paper)
  6. concentrationconcentrated
  7. custompurified on silica gel (2-8% MeOH in DCM)

Sources & evidence

ORD record
ord-40f0b8cbd2cd468ba7220508d989dc70
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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