Potassium Hydroxide → HCID 21913862, compound

HRID 1352542Notes

Reaction equation

HRID 1352542 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][N:11]1[C:19]2[C:18]([CH3:20])=[C:17]([CH3:21])[N:16]=[C:15](OC3C=CC=CC=3)[C:14]=2[N:13]=[C:12]1[CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+:34].[OH-].[K+]>>[CH2:1]([O:8][CH2:9][CH2:10][N:11]1[C:19]2[C:18]([CH3:20])=[C:17]([CH3:21])[N:16]=[C:15]([NH2:34])[C:14]=2[N:13]=[C:12]1[CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 14797Potassium HydroxideHCID 517165Ammonium AcetateHCID 21913064HCID 21913064, compound

Product 1

HCID 21913862HCID 21913862, compoundYield 55%

Conditions

Temperature
150 °C

Procedure

1-[2-(Benzyloxy)ethyl]-2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridine (5.113 g, 13.195 mmol) from Part A and ammonium acetate (51 g) were combined in a dried glass pressure flask under nitrogen. The flask was sealed and heated to 150° C. for 46 hours. The reaction was complete, and the resulting solution was cooled and basified to a pH of about 12 with 1 N potassium hydroxide. The basic solution was extracted with dichloromethane (3×), and the organic layers were combined, washed with water (3×) and brine (3×), dried with magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting oil was triturated with diethyl ether, and the resulting solids were filtered off. NMR analysis of the solids indicated residual phenol. The solids were dissolved in ethyl acetate. The ethyl acetate solution was washed with 1 N potassium hydroxide (4×), water (3×) and brine (3×), dried with magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting oil was diluted with diethyl ether, and after several hours the resulting crystals were filtered off and rinsed with diethyl ether. The resulting solids, which by NMR analysis were free of the phenol, were dried at 60° C. for 17 hours under high vacuum to provide 2.2515 g of 1-[2-(benzyloxy)ethyl]-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-4-amine, m.p. 136.8–137.5° C.

Workup

  1. customThe flask was sealed
  2. temperaturethe resulting solution was cooled
  3. extractionThe basic solution was extracted with dichloromethane (3×)
  4. washwashed with water (3×) and brine (3×)
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting oil was triturated with diethyl ether
  9. filtrationthe resulting solids were filtered off
  10. dissolutionThe solids were dissolved in ethyl acetate
  11. washThe ethyl acetate solution was washed with 1 N potassium hydroxide (4×), water (3×) and brine (3×)
  12. dry with materialdried with magnesium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated under reduced pressure
  15. additionThe resulting oil was diluted with diethyl ether
  16. filtrationafter several hours the resulting crystals were filtered off
  17. washrinsed with diethyl ether
  18. customwere dried at 60° C. for 17 hours under high vacuum

Sources & evidence

ORD record
ord-28fb9945668e4ee0b65550d8946f8595
Source dataset
uspto-grants-2007_05
Patent number
US07220758B2

Reaction notes

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