Hydrochloric Acid → HCID 15171569, compound

HRID 728169Notes

Reaction equation

HRID 728169 reaction equation
[CH2:1]([NH:3][C:4]1[O:5][C:6]2[CH:12]=[C:11]([CH2:13][CH2:14][C:15]3[N:16]=[C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][N:18]4[C:23]=3[CH3:24])[CH:10]=[CH:9][C:7]=2[N:8]=1)[CH3:2].Cl>[Pd].CO>[CH2:1]([NH:3][C:4]1[O:5][C:6]2[CH:12]=[C:11]([CH2:13][CH2:14][C:15]3[N:16]=[C:17]4[CH2:22][CH2:21][CH2:20][CH2:19][N:18]4[C:23]=3[CH3:24])[CH:10]=[CH:9][C:7]=2[N:8]=1)[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 15684578HCID 15684578, compound

Product 1

HCID 15171569HCID 15171569, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on carbon (0.2 g) was added to a mixture of 2-ethylamino-6-[2-(3-methylimidazo[1,2-a]pyridin-2-yl)ethyl]benzoxazole (0.5 g) in methanol (10 ml) and 1N-hydrochloric acid (10 ml) and the mixture was subjected to catalytic reduction at ambient temperature under atmospheric pressure. The catalyst was removed by filtration and the filtrate was evaporated in vacuo. To the residue was added a mixture of ethyl acetate and water and the mixture was adjusted to pH 8 with 20% aqueous potassium carbonate. The separated organic layer was washed with brine and dried over magnesium sulfate. The solvent was concentration and the residue was triturated with diethyl ether. The precipitate was collected by filtration and dried to give 2-ethylamino-6-[2-(3-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)-ethyl]benzoxazole (0.41 g).

Workup

  1. customwas subjected to catalytic reduction at ambient temperature under atmospheric pressure
  2. customThe catalyst was removed by filtration
  3. customthe filtrate was evaporated in vacuo
  4. additionTo the residue was added
  5. additiona mixture of ethyl acetate and water
  6. washThe separated organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentration
  9. customthe residue was triturated with diethyl ether
  10. filtrationThe precipitate was collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-1ecf043a98584c278162d4e589c7d7d2
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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