Hydrochloric Acid → HCID 15684566, compound

HRID 728160Notes

Reaction equation

HRID 728160 reaction equation
[NH2:1][C:2]1[O:3][C:4]2[CH:10]=[C:9]([CH2:11][CH2:12][C:13]3[N:14]=[C:15]4[CH:20]=[C:19]([NH:21]C(OC(C)(C)C)=O)[CH:18]=[CH:17][N:16]4[C:29]=3[CH3:30])[CH:8]=[CH:7][C:5]=2[N:6]=1.Cl>C(O)C>[NH2:1][C:2]1[O:3][C:4]2[CH:10]=[C:9]([CH2:11][CH2:12][C:13]3[N:14]=[C:15]4[CH:20]=[C:19]([NH2:21])[CH:18]=[CH:17][N:16]4[C:29]=3[CH3:30])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15171559HCID 15171559, compound

Product 1

HCID 15684566HCID 15684566, compoundYield 39.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 2-amino-6-[2-(3-methyl-7-tertbutoxycarbonylaminoimidazo[1,2-a]pyridin-2-yl)ethyl]benzoxazole (0.8 g) and conc. hydrochloric acid (0.9 ml) in ethanol (20 ml) was heated under refluxed for 1 hour. The mixture was ice-cooling and the isolated precipitate was collected by filtration. To a precipitate was added a mixture of ethyl acetate, tetrahydrofuran and water, and the mixture was adjusted to pH 8.5 with 20% aqueous potassium carbonate solution with salting-out technique. The separated organic layer was washed with brine and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was triturated with a solution of ethyl acetate and diethyl ether, and the precipitate was collected by filtration to give 2-amino-6-[2-(7-amino-3-methylimidazo[1,2-a]pyridin-2-yl)ethyl]benzoxazole (0.24 g).

Workup

  1. temperaturewas heated
  2. temperatureunder refluxed for 1 hour
  3. temperaturecooling
  4. filtrationthe isolated precipitate was collected by filtration
  5. additionTo a precipitate was added
  6. additiona mixture of ethyl acetate, tetrahydrofuran and water
  7. washThe separated organic layer was washed with brine
  8. dry with materialdried over magnesium sulfate
  9. customEvaporation of the solvent
  10. customgave a residue, which
  11. customwas triturated with a solution of ethyl acetate and diethyl ether
  12. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-3b0d0058d709473f8e4f871f23cd7f23
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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