Hydrochloric Acid → 8-(cyclohexylmethoxy)-2-methyl-N-(2-oxoethyl)imidazolo[1,2-a]pyridine-3-carboxamide

HRID 64412Notes

Reaction equation

HRID 64412 reaction equation
[CH:1]1([CH2:7][O:8][C:9]2[C:10]3[N:11]([C:15]([C:19]([NH:21][CH2:22][CH:23](OC)[O:24]C)=[O:20])=[C:16]([CH3:18])[N:17]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.C(OCC)(=O)C>O1CCOCC1.[Cl-].[Na+].O>[CH:1]1([CH2:7][O:8][C:9]2[C:10]3[N:11]([C:15]([C:19]([NH:21][CH2:22][CH:23]=[O:24])=[O:20])=[C:16]([CH3:18])[N:17]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 867134218-(cyclohexylmethoxy)-N-(2,2-dimethoxyethyl)-2-methylimidazolo[1,2-a]pyridine-3-carboxamide

Product 1

HCID 867134208-(cyclohexylmethoxy)-2-methyl-N-(2-oxoethyl)imidazolo[1,2-a]pyridine-3-carboxamideYield 94%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 200 mg of 8-(cyclohexylmethoxy)-N-(2,2-dimethoxyethyl)-2-methylimidazolo[1,2-a]pyridine-3-carboxamide in 2 mL of dioxane was added 6 M hydrochloric acid, followed by stirring for 7 hours. To the reaction mixture were added saturated brine and ethyl acetate to carry out a layer separation operation. To the obtained aqueous layer was added a 1 M aqueous sodium hydroxide solution, and the resulting solid was collected by filtration and dried to obtain 165 mg of 8-(cyclohexylmethoxy)-2-methyl-N-(2-oxoethyl)imidazolo[1,2-a]pyridine-3-carboxamide.

Workup

  1. customa layer separation operation
  2. additionTo the obtained aqueous layer was added a 1 M aqueous sodium hydroxide solution
  3. filtrationthe resulting solid was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-5865e51a6ecc45eca8d6a4d7f0bdde17
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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