Hydrochloric Acid → (1S,2R)-1-({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)-5-methylindane-2-carboxylic acid

HRID 64490Notes

Reaction equation

HRID 64490 reaction equation
[CH:1]1([CH2:7][O:8][C:9]2[C:10]3[N:11]([C:15]([C:19]([NH:21][C@@H:22]4[C:30]5[C:25](=[CH:26][C:27]([CH3:31])=[CH:28][CH:29]=5)[CH2:24][C@H:23]4[C:32]([O:34]C)=[O:33])=[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>O1CCOCC1>[CH:1]1([CH2:7][O:8][C:9]2[C:10]3[N:11]([C:15]([C:19]([NH:21][C@@H:22]4[C:30]5[C:25](=[CH:26][C:27]([CH3:31])=[CH:28][CH:29]=5)[CH2:24][C@H:23]4[C:32]([OH:34])=[O:33])=[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

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86713524methyl (1S,2R)-1-({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)-5-methylindane-2-carboxylate

Product 1

HCID 86713523(1S,2R)-1-({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)-5-methylindane-2-carboxylic acidYield 87.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 149 mg of methyl (1S,2R)-1-({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)-5-methylindane-2-carboxylate in 6 ml of dioxane was added 6 ml of 3 M hydrochloric acid, followed by stirring at 80° C. for 4 hours. After leaving to be cooled, the solvent was evaporated under reduced pressure, and then to the obtained residue were added a saturated aqueous sodium hydrogen carbonate solution, an aqueous citric acid solution, and chloroform to carry out a layer separation operation. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. To the obtained residue was added diisopropyl ether, and the insoluble material was collected by filtration and dried to obtain 126 mg of (1S,2R)-1-({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)-5-methylindane-2-carboxylic acid.

Workup

  1. customAfter leaving
  2. temperatureto be cooled
  3. customthe solvent was evaporated under reduced pressure
  4. additionto the obtained residue were added a saturated aqueous sodium hydrogen carbonate solution
  5. customa layer separation operation
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. additionTo the obtained residue was added diisopropyl ether
  9. filtrationthe insoluble material was collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-37450ce4497e4459bf6732c3fd1010a4
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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