Water → Ethyl 8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate

HRID 923453Notes

Reaction equation

HRID 923453 reaction equation
[CH:1]1([CH2:7][O:8][C:9]2[C:10]([NH2:15])=[N:11][CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH:17]([C:23](=O)[CH3:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19].C(N(CC)CC)C.O>C1(C)C=CC=CC=1.CCCCCC.C(OCC)(=O)C>[CH:1]1([CH2:7][O:8][C:9]2[C:10]3[N:11]([C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:23]([CH3:24])[N:15]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

8

Reactant 4

HCID 962WaterHCID 8471Triethylamine2×HCID 11858Ethyl 2-chloroacetoacetate2×HCID 138258903-(Cyclohexylmethoxy)pyridin-2-amine

Product 1

HCID 14676222Ethyl 8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5.8 g of 3-(cyclohexylmethoxy)pyridin-2-amine in 100 ml of toluene were added 4.3 ml of ethyl 2-chloro-3-oxobutanoate and 4.3 ml of triethylamine, followed by stirring overnight under heating to reflux. To the reaction mixture were added 1 ml of ethyl 2-chloro-3-oxobutanoate and 1 ml of triethylamine, followed by stirring for 6.5 hours under heating to reflux. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and the solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography. To the purified product thus obtained were added ethyl acetate and hexane, followed by heating and stirring, and then stirring under ice-cooling. The resulting solid was collected by filtration to obtain 4.0 g of ethyl 8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate.

Workup

  1. temperatureunder heating to reflux
  2. stirringby stirring for 6.5 hours
  3. temperatureunder heating to reflux
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was then evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography
  8. customTo the purified product thus obtained
  9. temperatureby heating
  10. stirringstirring
  11. stirringstirring under ice-
  12. temperaturecooling
  13. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-dbaf2241df664af2a717c1d1507ae869
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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