Methanol → 8-(cyclohexylmethoxy)-N-[(3-hydroxypropyl)sulfonyl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide

HRID 64477Notes

Reaction equation

HRID 64477 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][S:8]([NH:11][C:12]([C:14]1[N:18]2[CH:19]=[CH:20][CH:21]=[C:22]([O:23][CH2:24][CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[C:17]2=[N:16][C:15]=1[CH3:31])=[O:13])(=[O:10])=[O:9])(=O)C.CO.[OH-].[Na+]>C1COCC1>[CH:25]1([CH2:24][O:23][C:22]2[C:17]3[N:18]([C:14]([C:12]([NH:11][S:8]([CH2:7][CH2:6][CH2:5][OH:4])(=[O:10])=[O:9])=[O:13])=[C:15]([CH3:31])[N:16]=3)[CH:19]=[CH:20][CH:21]=2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 867135043-[({[8-(Cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)sulfonyl]propyl acetate

Product 1

HCID 867135058-(cyclohexylmethoxy)-N-[(3-hydroxypropyl)sulfonyl]-2-methylimidazo[1,2-a]pyridine-3-carboxamideYield 34.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 130 mg of 3-[({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)sulfonyl]propyl acetate were added 2 ml of methanol, 2 ml of THF, and 1 ml of a 1 M aqueous sodium hydroxide solution, followed by stirring for 8.5 hours. The solvent was evaporated under reduced pressure and to the obtained residue were added water and 1 M hydrochloric acid. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography. To the obtained purified product were added ethyl acetate and hexane, followed by stirring. The resulting solid was collected by filtration and dried to obtain 41 mg of 8-(cyclohexylmethoxy)-N-[(3-hydroxypropyl)sulfonyl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide.

Workup

  1. customThe solvent was evaporated under reduced pressure and to the obtained residue
  2. additionwere added water and 1 M hydrochloric acid
  3. customThe solvent was evaporated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography
  5. customTo the obtained purified product
  6. additionwere added ethyl acetate and hexane
  7. stirringby stirring
  8. filtrationThe resulting solid was collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-d9c72c258f9c4cdaa8531031a2130514
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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