Sodium hydride → 4-(N-t-butyloxycarbonylmethyloxyethyl-N-methyl-aminocarbonyl)-3-(4-t-butylphenyl)-1-(4-cyanophenyl)-2-methyl-2H-pyrazol-5-one

HRID 1740090Notes

Reaction equation

HRID 1740090 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([CH3:32])[N:13]([C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=3)[C:14](=[O:23])[C:15]=2[C:16]([N:18]([CH2:20][CH2:21][OH:22])[CH3:19])=[O:17])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36].[H-].[Na+].[Cl-].[NH4+]>O1CCCC1>[C:38]([O:37][C:35]([CH2:34][O:22][CH2:21][CH2:20][N:18]([CH3:19])[C:16]([C:15]1[C:14](=[O:23])[N:13]([C:24]2[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=2)[N:12]([CH3:32])[C:11]=1[C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:10][CH:9]=1)=[O:17])=[O:36])([CH3:41])([CH3:40])[CH3:39]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 79177tert-Butyl bromoacetateHCID 154355063-(4-t-butylphenyl)-1-(4-cyanophenyl)-4-(N-hydroxyethyl-N-methyl-aminocarbonyl)-2-methyl-2H-pyrazol-5-one

Product 1

HCID 154355074-(N-t-butyloxycarbonylmethyloxyethyl-N-methyl-aminocarbonyl)-3-(4-t-butylphenyl)-1-(4-cyanophenyl)-2-methyl-2H-pyrazol-5-oneYield 39.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 200 mg of 3-(4-t-butylphenyl)-1-(4-cyanophenyl)-4-(N-hydroxyethyl-N-methyl-aminocarbonyl)-2-methyl-2H-pyrazol-5-one, 4 ml of tetrahydrofuran and 108 mg of t-butyl bromoacetate, 12.2 mg of sodium hydride was added at 0° C., and the resulting reaction solution was refluxed under heating for 3 days. After the reaction solution was cooled to room temperature, saturated aqueous ammonium chloride was added, and the reaction solution was extracted with chloroform. The extract was washed with 1N hydrochloric acid and saturated aqueous sodium chloride successively and dried over anhydrous sodium sulfate. The insolubles were filtered off, and the filtrate was concentrated. The resulting residue was recrystallized in chloroform-ether-hexane to give 100 mg of the title compound as colorless crystals.

Workup

  1. additionwas added at 0° C.
  2. customthe resulting reaction solution
  3. temperaturewas refluxed
  4. temperatureunder heating for 3 days
  5. extractionthe reaction solution was extracted with chloroform
  6. washThe extract was washed with 1N hydrochloric acid and saturated aqueous sodium chloride successively
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationThe insolubles were filtered off
  9. concentrationthe filtrate was concentrated
  10. customThe resulting residue was recrystallized in chloroform-ether-hexane

Sources & evidence

ORD record
ord-9222feb102e34c0090b38900caa21d24
Source dataset
uspto-grants-1999_10
Patent number
US05968967

Reaction notes

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