Ammonia → 1-(3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridin-6-yl)ethanone

HRID 2409051Notes

Reaction equation

HRID 2409051 reaction equation
C([O:3][C:4]([C:6]1[N:11]=[CH:10][C:9]2[N:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[CH:13]=[N:14][C:8]=2[CH:7]=1)=[CH2:5])C.Cl.N>CO>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][N:12]2[C:9]3[CH:10]=[N:11][C:6]([C:4](=[O:3])[CH3:5])=[CH:7][C:8]=3[N:14]=[CH:13]2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 866898606-(1-ethoxyvinyl)-3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridine

Product 1

HCID 866898611-(3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridin-6-yl)ethanoneYield 75.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6-(1-ethoxyvinyl)-3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridine (440 mg, 1.42 mmol) in MeOH (2 mL) was added an aqueous solution of HCl (1N, 0.5 mL) and stirred at RT for 30 min. To the reaction mixture was added an aqueous ammonia solution (35%) until the pH was approximately 8. The aqueous solution was extracted with EtOAc (50 mL×3). The combined extracts were washed with water and brine, dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by SiO2 chromatography eluting with petroleum ether:EtOAc (1:1) to afford 300 mg (75%) of 1-(3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridin-6-yl)ethanone as a white solid. MS (ESI): m/z=282.3 [M+1]+.

Workup

  1. extractionThe aqueous solution was extracted with EtOAc (50 mL×3)
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by SiO2 chromatography
  7. washeluting with petroleum ether:EtOAc (1:1)

Sources & evidence

ORD record
ord-31f0b57e0bec4a31a921adba55714fa2
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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