Dimethylformamide → HCID 18463754, compound

HRID 2231127Notes

Reaction equation

HRID 2231127 reaction equation
[H-].[Na+].CN(C)C=O.[CH3:8][C:9]1[CH:10]=[C:11]([C:15]2[NH:19][C:18]([C:20]([F:23])([F:22])[F:21])=[N:17][C:16]=2[C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=2)[CH:12]=[CH:13][CH:14]=1.[CH3:34][Si:35]([CH3:42])([CH3:41])[CH2:36][CH2:37][O:38][CH2:39]Cl>CCCCCC>[CH3:8][C:9]1[CH:10]=[C:11]([C:15]2[N:19]([CH2:39][O:38][CH2:37][CH2:36][Si:35]([CH3:42])([CH3:41])[CH3:34])[C:18]([C:20]([F:22])([F:23])[F:21])=[N:17][C:16]=2[C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=2)[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178424684HCID 178424684, compound

Product 1

HCID 18463754HCID 18463754, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Sodium hydride (60% in oil, 1.06 mmol, 42 mg) was washed with hexane (ca 2×1 ml), then covered with N,N-dimethyformamide (2.1 ml). 5-(3-Methylphenyl)-4-[4-(methylsulfonyl)phenyl]-2-trifluoromethyl-1H-imidazole (Example 59) (0.70 mmol, 268 mg) was added, with stirring. After 15 minutes, 2-(trimethylsilyl)ethoxymethyl chloride (SEM-Cl) (1.06 mmol, 0.19 ml) was added and the mixture was stirred overnight. The reaction was quenched with saturated ammonium chloride (ca. 4 drops), and concentrated in vacuo. The residue was subjected to chromatography (2:1 hexane: ethyl acetate) and concentrated to afford the title compound (284 mg, 79%) as an oil as a mixture of the two possible N alkylated isomers (by NMR).

Workup

  1. stirringthe mixture was stirred overnight
  2. customThe reaction was quenched with saturated ammonium chloride (ca. 4 drops)
  3. concentrationconcentrated in vacuo
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-860018251c81400b917b7a82a808e7d7
Source dataset
uspto-grants-2002_07
Patent number
US06426360B1

Reaction notes

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