Water → HCID 68478407, compound

HRID 2194714Notes

Reaction equation

HRID 2194714 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH2:12][C:13]1[CH:17]=[C:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:15]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:14]=1)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[C:31](Cl)(=[O:33])[CH3:32].O>O1CCCC1.CN(C)C=O>[C:7]([O:6][C:5](=[O:11])[N:4]([CH2:12][C:13]1[CH:17]=[C:16]([N:18]([C:31](=[O:33])[CH3:32])[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:15]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:14]=1)[CH3:3])([CH3:10])([CH3:8])[CH3:9]

Participants

7

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 68410427HCID 68410427, compound

Product 1

HCID 68478407HCID 68478407, compoundYield 69.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (17 mg) in tetrahydrofuran (2 mL) and N,N-dimethylformamide (1 mL) was added tert-butyl methyl{[1-phenyl-5-(phenylamino)-1H-pyrazol-3-yl]methyl}carbamate (108 mg). After stirring at room temperature for 15 min, acetyl chloride (45 mg) was added, and the mixture was further stirred for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=7:1→3:1) to give the title compound as a colorless oil (yield 83 mg, yield 69%).

Workup

  1. stirringthe mixture was further stirred for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=7:1→3:1)

Sources & evidence

ORD record
ord-db702245ca954d9e90b499860274a5c9
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

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