Hydrochloric Acid → HCID 178510547, compound

HRID 2053812Notes

Reaction equation

HRID 2053812 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([CH2:11][NH:12]C(=O)C)[NH:8][C:5]2=[N:6][CH:7]=1.Cl>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([CH2:11][NH2:12])[NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178474651HCID 178474651, compound

Product 1

HCID 178510547HCID 178510547, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

2.03 g (7.54 mmol) of N-(6-bromo-3H-imidazo[4,5-b]pyridin-2-yl)methylacetamide is combined with 30 mL of 6 molar hydrochloric acid solution in 15 mL of ethanol and heated to 40° C. for 2 hours. After cooling to ambient temperature, the mixture is extracted with dichloromethane, and the organic phase is extracted with 5% sodium hydrogen carbonate solution. The aqueous phase is concentrated in vacuo and the residue treated with diethyl ether. After the solvent has been eliminated in vacuo the residue is combined with 30 mL of 6 molar hydrochloric acid solution and heated to 50° C. for 16 hours. After elimination of the solvent, the residue is twice taken up in methanol and in each case concentrated in vacuo. The crystals formed are washed with methanol and dried at 50° C. Yield: 560 mg (28%; hydrochloride); Rf value: 0.15 (silica gel; dichloromethane/ethanol=9:1+2% ammonia solution); C7H7BrN4 x HCl (227.06/263.53); mass spectrum: (M−H)−=225/227 (bromine isotope).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. extractionthe mixture is extracted with dichloromethane
  3. extractionthe organic phase is extracted with 5% sodium hydrogen carbonate solution
  4. concentrationThe aqueous phase is concentrated in vacuo
  5. additionthe residue treated with diethyl ether
  6. temperatureheated to 50° C. for 16 hours
  7. concentrationconcentrated in vacuo
  8. customThe crystals formed
  9. washare washed with methanol
  10. customdried at 50° C

Sources & evidence

ORD record
ord-7cd3ee40c90c4dac849e01d15c1e3821
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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