HCID 58765587, compound → HCID 178418884, compound

HRID 860138Notes

Reaction equation

HRID 860138 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][C:10]2[N:11]=[C:12]([CH3:23])[N:13](COCC[Si](C)(C)C)[CH:14]=2)[CH:5]=[CH:4][N:3]=1.CC1C=C(C#CC2N(COCC[Si](C)(C)C)C(C)=NC=2)C=CN=1>CCO.Cl>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][C:10]2[N:11]=[C:12]([CH3:23])[NH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 58765587HCID 58765587, compoundHCID 67552189HCID 67552189, compound

Product 1

HCID 178418884HCID 178418884, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

2-Methyl-4-[2-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-4-ylethynyl]-pyridine and 2-methyl-4-[2-methyl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazol-4-ylethynyl]-pyridine (2.85 g, 8.7 mmol) were dissolved in 50 mL EtOH saturated with HCl. The reaction mixture was stirred at RT overnight. The solvent was evaporated. The residue was taken up in 50 mL water and adjusted to pH7 by addition of sodium hydroxide. The aqueous phase was extracted three times with ethyl acetate (70 mL each). The combined organic extracts were dried with magnesium sulfate, filtered and evaporated. The crude product was purified by flash chromatography on silica gel (methylene chloride/methanol 100:5→85:15 gradient) and the desired compound was obtained as an off-white foam (1.19 g, 69%), MS: m/e=198.2 (M+H+). Method A2:

Workup

  1. customThe solvent was evaporated
  2. additionadjusted to pH7 by addition of sodium hydroxide
  3. extractionThe aqueous phase was extracted three times with ethyl acetate (70 mL each)
  4. dry with materialThe combined organic extracts were dried with magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by flash chromatography on silica gel (methylene chloride/methanol 100:5→85:15 gradient)

Sources & evidence

ORD record
ord-ddac01acdbde4728961905eb8a1dce96
Source dataset
uspto-grants-2006_12
Patent number
US07153874B2

Reaction notes

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