Hydrochloric Acid → HCID 86718181, compound

HRID 1624098Notes

Reaction equation

HRID 1624098 reaction equation
[OH-].[Na+].[CH:3]1([CH2:9][O:10][C:11]2[C:12]3[N:13]([C:17]([C:22]([O:24]CC)=[O:23])=[C:18]([CH2:20][CH3:21])[N:19]=3)[CH:14]=[CH:15][CH:16]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Cl>O1CCOCC1.ClCCl>[CH:3]1([CH2:9][O:10][C:11]2[C:12]3[N:13]([C:17]([C:22]([OH:24])=[O:23])=[C:18]([CH2:20][CH3:21])[N:19]=3)[CH:14]=[CH:15][CH:16]=2)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86718182HCID 86718182, compound

Product 1

HCID 86718181HCID 86718181, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

0.8 ml of 2N aqueous sodium hydroxide solution was added to a solution of 26 mg (0.082 mmol) of ethyl 8-(cyclohexylmethoxy)-2-ethylimidazo[1,2-a]pyridine-3-carboxylate in 1.15 ml of dioxane, and the mixture was stirred at room temperature overnight. The mixture was then acidified with 1.5 ml of 6N aqueous hydrochloric acid, diluted with 5 ml of dichloromethane and filtered over an Extrelut® cartridge. The cartridge was washed with 30 ml of dichloromethane, the filtrate was concentrated and the residue formed was dried under high vacuum. This gave 24 mg (97% of theory) of 8-(cyclohexylmethoxy)-2-ethylimidazo[1,2-a]pyridine-3-carboxylic acid as a crude product which was used as such for the next reaction.

Workup

  1. filtrationfiltered over an Extrelut® cartridge
  2. washThe cartridge was washed with 30 ml of dichloromethane
  3. concentrationthe filtrate was concentrated
  4. customthe residue formed
  5. customwas dried under high vacuum
  6. customsuch for the next reaction

Sources & evidence

ORD record
ord-66d30277668e448fa5a809bb1ffee933
Source dataset
uspto-grants-2014_07
Patent number
US08778964B2

Reaction notes

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