HCID 18461360, compound → HCID 18461408, compound

HRID 2303838Notes

Reaction equation

HRID 2303838 reaction equation
[OH:1][CH2:2][C:3]1[N:22]([CH3:23])[C:6]2=[N:7][C:8]([O:11][C:12]3[CH:17]=[C:16]([CH3:18])[C:15]([OH:19])=[C:14]([CH3:20])[C:13]=3[CH3:21])=[CH:9][CH:10]=[C:5]2[N:4]=1>N1C=CC=CC=1.C(OC(=O)C)(=O)C>[C:2]([O:1][CH2:2][C:3]1[N:22]([CH3:23])[C:6]2=[N:7][C:8]([O:11][C:12]3[CH:17]=[C:16]([CH3:18])[C:15]([O:19][C:8](=[O:11])[CH3:9])=[C:14]([CH3:20])[C:13]=3[CH3:21])=[CH:9][CH:10]=[C:5]2[N:4]=1)(=[O:1])[CH3:3]

Participants

4

Reactant 1

HCID 18461360HCID 18461360, compound

Product 1

HCID 18461408HCID 18461408, compoundYield 163.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 7918Acetic AnhydrideSolvent

Procedure

To 400 ml of a solution of 38.0 g of 2-hydroxymethyl-5-(4-hydroxy-2,3,5-trimethylphenoxy)-3-methyl-3H-imidazo[4,5-b]pyridine in pyridine, 69 ml of acetic anhydride were added dropwise under ice cooling. After stirring at room temperature for 3 hours, the reaction mixture was allowed to stand overnight at room temperature. The solvent was distilled off under reduced pressure. Water was added to the residue, followed by extraction with ethyl acetate. The extract was washed with saturated saline and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was separated and purified by chromatography through a silica gel column (eluting solvent n-hexane/ethyl acetate=1/2), whereby 39.5 g of the title compound were obtained.

Workup

  1. waitto stand overnight at room temperature
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionWater was added to the residue
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe extract was washed with saturated saline
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThe residue was separated
  9. custompurified by chromatography through a silica gel column (eluting solvent n-hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-bb062e9c398e4fb4bbf1af471c8ee47a
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

Loading…