Sodium Bicarbonate → 3-Cyanomethyl-2-methyl-8-(phenylpropoxy)-imidazo[1,2-a]pyridine

HRID 544453Notes

Reaction equation

HRID 544453 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.Cl[CH:19]([C:23](=O)[CH3:24])[CH2:20][C:21]#[N:22].C(=O)(O)[O-].[Na+]>C(COC)OC>[C:21]([CH2:20][C:19]1[N:3]2[CH:4]=[CH:5][CH:6]=[C:7]([O:8][CH2:9][CH2:10][CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:2]2=[N:1][C:23]=1[CH3:24])#[N:22]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 127582783-(3-Phenylpropoxy)pyridin-2-amineHCID 139002363-Chloro-4-oxopentanenitrile

Product 1

HCID 204590053-Cyanomethyl-2-methyl-8-(phenylpropoxy)-imidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 5.3 g of 2-amino-3-(3-phenylpropoxy)pyridine, 3.2 g of 3-chloro-4-oxopentanonitrile, 2.0 g sodium bicarbonate, and 50 ml dimethoxyethane was heated at reflux for 24 hrs., then stirred at room temperature 66 hrs. the solvent was removed in vacuo, the brown residue was taken up in 100 ml methylene chloride, filtered, dried over potassium carbonate and evaporated in vacuo to leave a brown gum residue. The residue was chromatographed on silica gel using first chloroform, then switching to 1:1 chloroform/ethyl acetate. The early eluates were combinedand evaporated and the resultant residue crystallized from isopropyl/ether to give the title compound (m.p. 143°-145° C.).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hrs
  3. customthe solvent was removed in vacuo
  4. filtrationfiltered
  5. dry with materialdried over potassium carbonate
  6. customevaporated in vacuo
  7. customto leave a brown gum residue
  8. customThe residue was chromatographed on silica gel using first chloroform
  9. customThe early eluates were combinedand evaporated
  10. customthe resultant residue crystallized from isopropyl/ether

Sources & evidence

ORD record
ord-06372511cbfa412da2d65ad8471dc434
Source dataset
uspto-grants-1984_05
Patent number
US04450164

Reaction notes

Loading…