Methyl iodide → 4-(2,2-dimethylbutyl)-2-{2-[4-(5-fluoropyridin-2-yl)phenyl]-1-methoxyethyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide

HRID 1881421Notes

Reaction equation

HRID 1881421 reaction equation
[H-].[Na+].CC(C)(C)CC1N=[C:8](C(O)CC2C=CC(C3C=CC=CN=3)=CC=2)[N:9]([S:11](N(C)C)(=[O:13])=[O:12])[CH:10]=1.[CH3:34]I.[CH3:36][C:37]([CH3:62])([CH2:60][CH3:61])[CH2:38][C:39]1[N:40]=[C:41]([CH:44]([OH:59])[CH2:45][C:46]2[CH:51]=[CH:50][C:49]([C:52]3[CH:57]=[CH:56][C:55]([F:58])=[CH:54][N:53]=3)=[CH:48][CH:47]=2)[NH:42][CH:43]=1>>[CH3:36][C:37]([CH3:62])([CH2:60][CH3:61])[CH2:38][C:39]1[N:40]=[C:41]([CH:44]([O:59][CH3:34])[CH2:45][C:46]2[CH:51]=[CH:50][C:49]([C:52]3[CH:57]=[CH:56][C:55]([F:58])=[CH:54][N:53]=3)=[CH:48][CH:47]=2)[N:42]([S:11]([N:9]([CH3:10])[CH3:8])(=[O:13])=[O:12])[CH:43]=1

Participants

5

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66705591HCID 66705591, compoundHCID 1784424641-[4-(2,2-dimethylbutyl)-1H-imidazol-2-yl]-2-[4-(5-fluoropyridin-2-yl)phenyl]ethanol

Product 1

HCID 667057254-(2,2-dimethylbutyl)-2-{2-[4-(5-fluoropyridin-2-yl)phenyl]-1-methoxyethyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide

Procedure

Sodium hydride (60 wt % in mineral oil) (50 mg, 1.25 mmol) was added to an ambient temperature solution of 4-(2,2-dimethylpropyl)-2-[1-hydroxy-2-(4-pyridin-2-ylphenyl)ethyl]-N,N-dimethyl-1H-imidazole-1-sulfonamide in N,N-dimethylformamide (for synthesis see example 11) (2 mL). After stirring at ambient temperature for 20 min, methyl iodide (50 μL, 0.8 mmol) was added. After stirring at ambient temperature for a further 2 h, the reaction mixture was quenched with saturated aqueous ammonium chloride and extracted with diethyl ether. The combined ethereal layers were dried (magnesium sulfate) and concentrated in vacuo to afford 4-(2,2-dimethylbutyl)-2-{2-[4-(5-fluoropyridin-2-yl)phenyl]-1-methoxyethyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide which was used in the subsequent step without further purification.

Workup

  1. stirringAfter stirring at ambient temperature for a further 2 h
  2. customthe reaction mixture was quenched with saturated aqueous ammonium chloride
  3. extractionextracted with diethyl ether
  4. dry with materialThe combined ethereal layers were dried (magnesium sulfate)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7bb595bd8e91485fa6dd0ed2018a6952
Source dataset
uspto-grants-2012_11
Patent number
US08318767B2

Reaction notes

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