2,5-Dimethoxytetrahydrofuran → HCID 22485236, compound

HRID 2181043Notes

Reaction equation

HRID 2181043 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:11]3=[N:12][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:15]=[C:10]3[N:9]=[C:8]2[CH3:20])=[C:4]([Cl:23])[CH:3]=1.CO[CH:26]1[CH2:30][CH2:29][CH:28](OC)O1>C(O)(=O)C>[Cl:23][C:4]1[CH:3]=[C:2]([N:1]2[CH:26]=[CH:30][CH:29]=[CH:28]2)[CH:22]=[CH:21][C:5]=1[CH2:6][N:7]1[C:11]2=[N:12][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:15]=[C:10]2[N:9]=[C:8]1[CH3:20]

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 22388007HCID 22388007, compound

Product 1

HCID 22485236HCID 22485236, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Methyl 3-(4-amino-2-chlorobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (1.00 g) was dissolved in acetic acid (5.0 ml) and 2,5-dimethoxytetrahydrofuran (420 mg) was added, which was followed by refluxing under heating for 2 hr. The reaction mixture was concentrated under reduced pressure and the residue was applied to silica gel column chromatography and eluted with chloroform:ethyl acetate=3:1. The objective fraction was concentrated under reduced pressure and ethyl acetate (10.0 ml) was added to the residue. After heating, the mixture was allowed to cool and the precipitated crystals were collected by filtration to give methyl 3-(2-chloro-4-(1-pyrrolyl)benzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (641 mg) as colorless crystals.

Workup

  1. temperatureby refluxing
  2. temperatureunder heating for 2 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. washeluted with chloroform
  5. concentrationThe objective fraction was concentrated under reduced pressure and ethyl acetate (10.0 ml)
  6. additionwas added to the residue
  7. temperatureAfter heating
  8. temperatureto cool
  9. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-c4040e6dd97240c7b0e6c22e3029ce92
Source dataset
uspto-grants-2005_05
Patent number
US06890934B2

Reaction notes

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