HCID 86704966, compound → HCID 68350583, compound

HRID 572154Notes

Reaction equation

HRID 572154 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([C:10]3[CH:33]=[CH:32][C:13]([O:14][C:15]4[N:19](COCC[Si](C)(C)C)[C:18]5[CH:28]=[CH:29][CH:30]=[CH:31][C:17]=5[N:16]=4)=[CH:12][CH:11]=3)=[CH:8][CH:7]=[CH:6][N:5]2[CH:34]=1>C(OCC)(=O)C.Cl>[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([C:10]3[CH:33]=[CH:32][C:13]([O:14][C:15]4[NH:19][C:18]5[CH:28]=[CH:29][CH:30]=[CH:31][C:17]=5[N:16]=4)=[CH:12][CH:11]=3)=[CH:8][CH:7]=[CH:6][N:5]2[CH:34]=1

Participants

3

Reactant 1

HCID 86704966HCID 86704966, compound

Product 1

HCID 68350583HCID 68350583, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

A mixture of 2-[4-(2-methylimidazo[1,2-a]pyridin-8-yl)phenoxy]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazole (0.57 g) and 4 M hydrogen chloride-ethyl acetate solution (20 ml) was heated under reflux for 3 hr. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was recrystallized from ethyl acetate to give the title compound (0.35 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution
  4. additionwas added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe extract was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-4245c6d26e4d4a83b69b62e6fba5590c
Source dataset
uspto-grants-2015_05
Patent number
US09029388B2

Reaction notes

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