Water → HCID 66939428, compound

HRID 1257366Notes

Reaction equation

HRID 1257366 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([C:15]2[N:16]=[C:17]([CH2:20][N:21]3[CH:25]=[C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:23]=[N:22]3)[S:18][CH:19]=2)[CH:12]=[CH:13][CH:14]=1)=[O:7].I[CH3:32].O>CN(C)C=O.O1CCCC1>[CH3:3][O:4][CH2:5][C:6]([N:8]([CH3:32])[C:9]1[CH:10]=[C:11]([C:15]2[N:16]=[C:17]([CH2:20][N:21]3[CH:25]=[C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:23]=[N:22]3)[S:18][CH:19]=2)[CH:12]=[CH:13][CH:14]=1)=[O:7]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58127684ethyl 1-[(4-{3-[(methoxyacetyl)amino]phenyl}-1,3-thiazol-2-yl)methyl]-1H-pyrazole-4-carboxylate

Product 1

HCID 66939428HCID 66939428, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere at 0° C., to a solution (2 mL) of sodium hydride (60% in mineral oil, 93 mg, 2.3 mmol) in N,N-dimethylformamide was added dropwise a solution (2 mL) of the compound (720 mg, 1.8 mmol) obtained in Example 26b in tetrahydrofuran, and the mixture was stirred at room temperature for 30 min. Then, iodomethane (0.22 mL, 3.6 mmol) was added to the reaction mixture and the mixture was stirred at room temperature for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was purified by column chromatography (hexane-ethyl acetate) to give the title compound (500 mg, 67%) as a colorless oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe resulting crude title compound was purified by column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-fae246070395444dab8960606010e75e
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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