Pyrazole → HCID 67491137, compound

HRID 571961Notes

Reaction equation

HRID 571961 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]2[CH2:17][CH2:16][CH2:15][C@@H:14]([N:18]3[CH:22]=[N:21][N:20]=[CH:19]3)[CH2:13]2)(=[O:10])=[O:9])=[C:4]([CH2:23][CH3:24])[CH:3]=1.[NH:25]1[CH:29]=[CH:28][CH:27]=[N:26]1.C(=NO)C1C(=CC=CC=1)O.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.[Cu-]=O>[CH2:23]([C:4]1[CH:3]=[C:2]([N:25]2[CH:29]=[CH:28][CH:27]=[N:26]2)[CH:7]=[CH:6][C:5]=1[S:8]([NH:11][C@H:12]1[CH2:17][CH2:16][CH2:15][C@@H:14]([N:18]2[CH:22]=[N:21][N:20]=[CH:19]2)[CH2:13]1)(=[O:10])=[O:9])[CH3:24]

Participants

7

Reactant 4

HCID 1048PyrazoleHCID 7200Salicylaldehyde oximeHCID 10796Cesium carbonateHCID 49869930HCID 49869930, compound

Product 1

HCID 67491137HCID 67491137, compound

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2a (39.6 mg, 0.096 mmol), pyrazole (49.0 mg, 0120 mmol), copper (1) oxide (16.0 mg, 0.112 mmol), salicylaldoxime (19.0 mg, 0.139 mmol) and cesium carbonate (255 mg, 0.783 mmol) in acetonitrile (500 μL) was placed in a sealed tube and heated in a microwave reactor at 120° C. for 30 min. After cooling to room temperature, the reaction mixture was partitioned between EtOAc and brine. The layers were separated, and the aqueous layer was extracted with EtOAc. The combined organics were filtered through a short column of Celite®, eluting copiously with EtOAc, and concentrated in vacuo. The crude residue was purified by preparative thin layer chromatography on silica gel (10% MeOH/DCM as eluent) to afford the title compound, 6a. m/z (ES) 401 (MH); IC50=68 nM

Workup

  1. customwas placed in a sealed tube
  2. temperatureAfter cooling to room temperature
  3. customthe reaction mixture was partitioned between EtOAc and brine
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with EtOAc
  6. filtrationThe combined organics were filtered through a short column of Celite®
  7. washeluting copiously with EtOAc
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified by preparative thin layer chromatography on silica gel (10% MeOH/DCM as eluent)

Sources & evidence

ORD record
ord-fd959ae262c04313b79a4c49fdd7a374
Source dataset
uspto-grants-2015_05
Patent number
US09029377B2

Reaction notes

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