Methyl iodide → HCID 18674171, compound

HRID 1635931Notes

Reaction equation

HRID 1635931 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]([CH3:15])[N:13]=[C:12]([NH:16][C:17](=[O:25])[CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:11]=2[C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)=[CH:6][CH:5]=1.[CH3:32]I>CN(C)C=O>[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]([CH3:15])[N:13]=[C:12]([N:16]([CH3:32])[C:17](=[O:25])[CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:11]=2[C:26]2[CH:27]=[CH:28][N:29]=[CH:30][CH:31]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69692723HCID 69692723, compound

Product 1

HCID 18674171HCID 18674171, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

While 2 1m of a dimethylformamide suspension containing 20 mg of 60% sodium hydride was being cooled with ice, 3 ml of a dimethylformamide solution containing 180 mg of 5-(4-fluorophenyl)-1-methyl-3-phenylacetylamino-4-(4-pyridyl)pyrazole was added dropwise thereto, followed by stirring at room temperature for 30 minutes. Then, 2 ml of a dimethylformamide solution containing 80 mg of methyl iodide was added dropwise thereto, followed by stirring at room temperature for 2 hours. After the dimethylformamide was distilled off under reduced pressure, the resulting residue was purified by column chromatography using 30 g of silica gel [with an elution solvent comprising chloroform-methanol (70:1)]. Thus, 149.2 mg (80% yield) of the title compound was obtained as pale-yellow crystals.

Workup

  1. additionwas added dropwise
  2. additionwas added dropwise
  3. stirringby stirring at room temperature for 2 hours
  4. distillationAfter the dimethylformamide was distilled off under reduced pressure
  5. customthe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-b3ce16af9c2643e5b09543a6f4eb0837
Source dataset
uspto-grants-2003_01
Patent number
US06511997B1

Reaction notes

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