Hydrochloric Acid → 1-ethyl-3-[4-(imidazo[1,2-a]pyridin-2-yloxy)phenyl]-6-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 587559Notes

Reaction equation

HRID 587559 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[N:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[N:5]([C:13]2[CH:33]=[CH:32][C:16]([O:17][C:18]3[N:19]=[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][N:21]4[C:26]=3C(OCC)=O)=[CH:15][CH:14]=2)[C:4]1=[O:34])[CH3:2].[OH-].[Na+].Cl>CCO>[CH2:1]([N:3]1[C:11]2[C:6](=[N:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[N:5]([C:13]2[CH:33]=[CH:32][C:16]([O:17][C:18]3[N:19]=[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][N:21]4[CH:26]=3)=[CH:15][CH:14]=2)[C:4]1=[O:34])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58577566ethyl 2-[4-(1-ethyl-6-methyl-2-oxo-1,2-dihydro-3H-imidazo[4,5-b]pyridin-3-yl)phenoxy]imidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 585774471-ethyl-3-[4-(imidazo[1,2-a]pyridin-2-yloxy)phenyl]-6-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-oneYield 80.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 2-[4-(1-ethyl-6-methyl-2-oxo-1,2-dihydro-3H-imidazo[4,5-b]pyridin-3-yl)phenoxy]imidazo[1,2-a]pyridine-3-carboxylate (62 mg) in EtOH (4 mL) was added sodium hydroxide (1.084 mL). The mixture was stirred at 50° C. for 2 h. Hydrochloric acid (2.168 mL) was added to the mixture, and the mixture was stirred at 60° C. for 10 h. The mixture was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, EtOAc/hexane) to give the title compound (42.0 mg) as a colorless oil.

Workup

  1. stirringthe mixture was stirred at 60° C. for 10 h
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography (silica gel, EtOAc/hexane)

Sources & evidence

ORD record
ord-7241901b102f4504899e57922813e851
Source dataset
uspto-grants-2016_01
Patent number
US09226921B2

Reaction notes

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