Water → HCID 68408884, compound

HRID 2194713Notes

Reaction equation

HRID 2194713 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].I[CH3:32].O>O1CCCC1.CN(C)C=O>[CH3:3][N:4]([CH2:12][C:13]1[CH:17]=[C:16]([N:18]([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)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:8])[CH3:9]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68410427HCID 68410427, compound

Product 1

HCID 68408884HCID 68408884, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (16 mg) in tetrahydrofuran (2 mL) and N,N-dimethylformamide (0.5 mL) was added tert-butyl methyl{[1-phenyl-5-(phenylamino)-1H-pyrazol-3-yl]methyl}carbamate (100 mg). After stirring at room temperature for 30 min, iodomethane (75 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=9:1→4:1) to give the title compound as a pale-brown oil (yield 67 mg, yield 65%).

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=9:1→4:1)

Sources & evidence

ORD record
ord-17e0f8d71ca74e97b69c8b7702fdc793
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

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