Methanol → HCID 67558459, compound

HRID 1416059Notes

Reaction equation

HRID 1416059 reaction equation
[I-].[K+].C[Si](Cl)(C)C.[CH2:8]([O:15][CH2:16][C:17]1[N:18]([CH2:34][C:35]2[CH:36]=[CH:37][C:38]([O:41]C)=[N:39][CH:40]=2)[C:19]([S:25][C:26]2[CH:31]=[C:30]([Cl:32])[CH:29]=[C:28]([Cl:33])[CH:27]=2)=[C:20]([CH:22]([CH3:24])[CH3:23])[N:21]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CO>C(#N)C>[CH2:8]([O:15][CH2:16][C:17]1[N:18]([CH2:34][C:35]2[CH:40]=[N:39][C:38](=[O:41])[CH2:37][CH:36]=2)[C:19]([S:25][C:26]2[CH:27]=[C:28]([Cl:33])[CH:29]=[C:30]([Cl:32])[CH:31]=2)=[C:20]([CH:22]([CH3:24])[CH3:23])[N:21]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 4875Potassium IodideHCID 6397ChlorotrimethylsilaneHCID 22130117HCID 22130117, compound

Product 1

HCID 67558459HCID 67558459, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 83 mg of potassium iodide in acetonitrile was added 64 μl of trimethylsilyl chloride under ice-cooling and stirring. The mixture was allowed to warm up, and after 10 minutes, 150 mg of 2-benzyloxymethyl-5-(3,5-dichlorophenylthio)-1-(2-methoxypyridin-5-ylmethyl)-4-isopropyl-1H-imidazole was added, and the mixture was stirred with heating at 60° C. After 1 hour, the solution was distilled off under reduced pressure, an aqueous sodium hydrogen carbonate solution was added, extracted with ethyl acetate, the extract was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate:methanol=10:1)to give 50 mg of 2-benzyloxymethyl-5-(3,5-dichlorophenylthio)-1-(5,6-dihydro-6-oxopyridin-3-ylmethyl)-4-isopropyl-1H-imidazole (115a)(yield 34%).

Workup

  1. temperaturecooling
  2. temperatureto warm up
  3. stirringthe mixture was stirred
  4. waitAfter 1 hour
  5. distillationthe solution was distilled off under reduced pressure
  6. additionan aqueous sodium hydrogen carbonate solution was added
  7. extractionextracted with ethyl acetate
  8. dry with materialthe extract was dried over sodium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue was purified by silica gel chromatography (ethyl acetate

Sources & evidence

ORD record
ord-7474f4c5e55949e4a0bfbb640e4f92b8
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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