Ammonium Acetate → HCID 10085926, compound

HRID 1352535Notes

Reaction equation

HRID 1352535 reaction equation
C([O-])(=O)C.[NH4+:5].[CH3:6][C:7]1[N:8]([CH2:25][CH2:26][O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:9]2[C:14]([CH3:15])=[C:13]([CH3:16])[N:12]=[C:11](OC3C=CC=CC=3)[C:10]=2[N:24]=1>C(OCC)(=O)C>[CH3:6][C:7]1[N:8]([CH2:25][CH2:26][O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:9]2[C:14]([CH3:15])=[C:13]([CH3:16])[N:12]=[C:11]([NH2:5])[C:10]=2[N:24]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 21913797HCID 21913797, compound

Product 1

HCID 10085926HCID 10085926, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A sealed tube containing anhydrous ammonium acetate (11.4 g) and 2,6,7-trimethyl-4-phenoxy-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]pyridine (1.14 g) from Part C was heated to 150° C. for 40 hours. The reaction was allowed to cool to room temperature. The resulting reaction mixture was then dissolved in ethyl acetate and washed with a saturated aqueous solution of sodium bicarbonate. The basic layer was washed twice with ethyl acetate. The organic layers were combined, dried with magnesium sulfate, and the solvents were removed under reduced pressure. The resulting orange solid was passed through a silica gel column using 94/6 dichloromethane/methanol as the eluant. Because NMR analysis indicated that the white solid contained ammonium acetate, the product was dissolved in chloroform and washed with 25% aqueous sodium hydroxide. The resulting basic aqueous layer was extracted twice with chloroform. The organic layers were combined, washed with water, dried with magnesium sulfate, and concentrated under reduced pressure. The resulting white solid was dried under vacuum at 60° C. for 24 hours to provide 2,6,7-trimethyl-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]pyridin-4-amine, m.p. 176.0–177.0° C.

Workup

  1. temperatureto cool to room temperature
  2. customThe resulting reaction mixture
  3. washwashed with a saturated aqueous solution of sodium bicarbonate
  4. washThe basic layer was washed twice with ethyl acetate
  5. dry with materialdried with magnesium sulfate
  6. customthe solvents were removed under reduced pressure
  7. dissolutionthe product was dissolved in chloroform
  8. washwashed with 25% aqueous sodium hydroxide
  9. extractionThe resulting basic aqueous layer was extracted twice with chloroform
  10. washwashed with water
  11. dry with materialdried with magnesium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customThe resulting white solid was dried under vacuum at 60° C. for 24 hours

Sources & evidence

ORD record
ord-16f68ac54e67490d84e6982ee8ee5d68
Source dataset
uspto-grants-2007_05
Patent number
US07220758B2

Reaction notes

Loading…