Methyl iodide → HCID 24859016, compound

HRID 237412Notes

Reaction equation

HRID 237412 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH:7][C:8]([NH:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:21]([F:24])([F:23])[F:22])[CH:19]=2)[N:14]=[CH:13][CH:12]=1)=[O:9].[H-].[Na+].[CH3:27]I>CN(C)C=O>[CH3:27][N:7]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][N:1]=1)[C:8]([NH:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:21]([F:24])([F:22])[F:23])[CH:19]=2)[N:14]=[CH:13][CH:12]=1)=[O:9]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 24858859HCID 24858859, compound

Product 1

HCID 24859016HCID 24859016, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 145 mg (0.44 mmol) of 1-pyrazin-2-yl-3-(6-trifluoromethyl-quinolin-4-yl)-urea (Example 14) and 16 mg (0.65 mmol) of sodium hydride in 10 ml of dimethylformamide was stirred at 0° C. for 10 min. Methyl iodide (93 mg, 0.65 mmol) was added and the solution was allowed to reach RT and stirred for a further 16 h. The solution was concentrated in vacuo, and partitioned between dichloromethane and water. The organic layer was washed 3 times with water, concentrated in vacuo and the material purified by chromatography. White solid. Amount 32 mg. Yield 21.2%.

Workup

  1. customto reach RT
  2. concentrationThe solution was concentrated in vacuo
  3. custompartitioned between dichloromethane and water
  4. washThe organic layer was washed 3 times with water
  5. concentrationconcentrated in vacuo
  6. customthe material purified by chromatography

Sources & evidence

ORD record
ord-66ebc15155ae4d228bd174247fcc2233
Source dataset
uspto-grants-2014_02
Patent number
US08642598B2

Reaction notes

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