Methyl iodide → HCID 68674706, compound

HRID 1927674Notes

Reaction equation

HRID 1927674 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([C:11]2[NH:12][C:13]([CH2:16][CH2:17][C:18]3[N:19]([S:29]([N:32]([CH3:34])[CH3:33])(=[O:31])=[O:30])[CH:20]=[C:21]([CH2:23][C:24]([CH3:28])([CH3:27])[CH2:25][CH3:26])[N:22]=3)=[N:14][N:15]=2)[CH:7]=[CH:8][C:9]=1[F:10].[CH3:35]I>CN(C=O)C>[F:3][C:4]1[CH:5]=[C:6]([C:11]2[N:12]=[C:13]([CH2:16][CH2:17][C:18]3[N:19]([S:29]([N:32]([CH3:33])[CH3:34])(=[O:30])=[O:31])[CH:20]=[C:21]([CH2:23][C:24]([CH3:27])([CH3:28])[CH2:25][CH3:26])[N:22]=3)[N:14]([CH3:35])[N:15]=2)[CH:7]=[CH:8][C:9]=1[F:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178442475HCID 178442475, compound

Product 1

HCID 68674706HCID 68674706, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (21 mg, 0.87 mmol) was added to a solution of 2-{2-[5-(3,4-difluorophenyl)-4H-1,2,4-triazol-3-yl]ethyl}-4-(2,2-dimethylbutyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide (135 mg, 0.29 mmol) in DMF (4 mL) at 0° C., and the reaction was stirred at rt for 30 min. Methyliodide (0.09 mL, 1.4 mmol) was added and stirring continued for 1 hr. The reaction mixture was partitioned between water and diethyl ether. The organic phase was washed with water and brine, dried (sodium sulfate) and concentrated to give a residue. Chromatography of the residue over silica gel (eluting with 60-100% ethyl acetate/hexane) afforded 2-{2-[3-(3,4-difluorophenyl)-1-methyl-1H-1,2,4-triazol-5-yl]ethyl}-4-(2,2-dimethylbutyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide as an off-white solid.

Workup

  1. stirringstirring
  2. waitcontinued for 1 hr
  3. customThe reaction mixture was partitioned between water and diethyl ether
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated
  7. customto give a residue

Sources & evidence

ORD record
ord-e432880c959d4730b1ea0b4c7fdd3072
Source dataset
uspto-grants-2012_05
Patent number
US08183275B2

Reaction notes

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