Hydrochloric Acid → 3-[4-(1H-benzimidazol-2-yloxy)phenyl]-1-ethyl-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one dihydrochloride

HRID 82555Notes

Reaction equation

[CH2:1]([N:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][C:10]=2[CH3:12])[N:5]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[N:24](COCC[Si](C)(C)C)[C:23]4[CH:33]=[CH:34][CH:35]=[CH:36][C:22]=4[N:21]=3)=[CH:15][CH:14]=2)[C:4]1=[O:37])[CH3:2].[ClH:38]>CCO>[ClH:38].[ClH:38].[NH:21]1[C:22]2[CH:36]=[CH:35][CH:34]=[CH:33][C:23]=2[N:24]=[C:20]1[O:19][C:16]1[CH:17]=[CH:18][C:13]([N:5]2[C:6]3=[N:7][CH:8]=[CH:9][C:10]([CH3:12])=[C:11]3[N:3]([CH2:1][CH3:2])[C:4]2=[O:37])=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 1-ethyl-7-methyl-3-{4-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]phenyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (0.090 g) and 2N HCl in EtOH (5.0 mL) was stirred at 60° C. for 10 h. After cooling to room temperature, the solvent was removed. The residue was recrystallized from EtOH-AcOEt to give 3-[4-(1H-benzimidazol-2-yloxy)phenyl]-1-ethyl-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one dihydrochloride (0.040 g).

Workup

temperatureAfter cooling to room temperature
customthe solvent was removed
customThe residue was recrystallized from EtOH-AcOEt

Sources & evidence

ORD record: ord-749617bd53144158affdf710d5759af3
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846713B2

Reaction notes

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