Hydrochloric Acid → 5-Methoxy-3-(3-methoxypropyl)-2-(piperidin-3-yl)-3H-imidazo[4,5-b]pyridine

HRID 1096616Notes

Reaction equation

HRID 1096616 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]2[N:9]([CH2:25][CH2:26][CH2:27][O:28][CH3:29])[C:10]([CH:12]3[CH2:17][CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13]3)=[N:11][C:6]2=[CH:5][CH:4]=1.Cl>CCO>[CH3:1][O:2][C:3]1[N:8]=[C:7]2[N:9]([CH2:25][CH2:26][CH2:27][O:28][CH3:29])[C:10]([CH:12]3[CH2:17][CH2:16][CH2:15][NH:14][CH2:13]3)=[N:11][C:6]2=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66785067tert-butyl 3-(5-methoxy-3-(3-methoxypropyl)-3H-imidazo[4,5-b]pyridin-2-yl)piperidine-1-carboxylate

Product 1

HCID 667864945-Methoxy-3-(3-methoxypropyl)-2-(piperidin-3-yl)-3H-imidazo[4,5-b]pyridineYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

tert-Butyl 3-(5-methoxy-3-(3-methoxypropyl)-3H-imidazo[4, 5-13]pyridin-2-yl)piperidine-1-carboxylate (33C) (1.19 mmol; 0.481 g) was added to a 100 mL round-bottomed flask equipped with a reflux condenser and stirring under nitrogen. EtOH (15 mL) and HCl (8M in H2O; 4 mL) were then added and the solution was heated to reflux for 15 min. Analysis of the reaction mixture by LC/MS indicated that the reaction was complete at this time. The ethanol was then removed in-vacuo. The resultant solution was extracted with EtOAc and a 10% aqueous K2CO3 solution. The organic layer was collected and dried with Na2SO4. This was then filtered and concentrated and dried in-vacuo affording 5-Methoxy-3-(3-methoxypropyl)-2-(piperidin-3-yl)-3H-imidazo[4,5-b]pyridine (330) as a brown oil. (1.15 mmol, 0.351 g, 97% yield). ESI-MS: m/z 305.1 (M+H)+.

Workup

  1. customequipped with a reflux condenser
  2. temperaturethe solution was heated
  3. temperatureto reflux for 15 min
  4. customThe ethanol was then removed in-vacuo
  5. extractionThe resultant solution was extracted with EtOAc
  6. customThe organic layer was collected
  7. dry with materialdried with Na2SO4
  8. filtrationThis was then filtered
  9. concentrationconcentrated
  10. customdried in-vacuo

Sources & evidence

ORD record
ord-3a158c59ca0849b8b4aedd92891cebb3
Source dataset
uspto-grants-2012_03
Patent number
US08138168B1

Reaction notes

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