Hydrochloric Acid → 3-[4-(1H-Benzimidazol-2-yloxy)phenyl]-1-ethyl-1H-pyrazolo[4,3-b]pyridine

HRID 573271Notes

Reaction equation

HRID 573271 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[N:23](COCC[Si](C)(C)C)[C:22]4[CH:32]=[CH:33][CH:34]=[CH:35][C:21]=4[N:20]=3)=[CH:14][CH:13]=2)=[N:4]1)[CH3:2].Cl.[OH-].[Na+]>CCO>[NH:23]1[C:22]2[CH:32]=[CH:33][CH:34]=[CH:35][C:21]=2[N:20]=[C:19]1[O:18][C:15]1[CH:16]=[CH:17][C:12]([C:5]2[C:6]3=[N:7][CH:8]=[CH:9][CH:10]=[C:11]3[N:3]([CH2:1][CH3:2])[N:4]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 866889571-Ethyl-3-{4-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]phenyl}-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 667281363-[4-(1H-Benzimidazol-2-yloxy)phenyl]-1-ethyl-1H-pyrazolo[4,3-b]pyridineYield 78.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-ethyl-3-{4-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]phenyl}-1H-pyrazolo[4,3-b]pyridine (510 mg), 6 M HCl aqueous solution (5 mL), and EtOH (5 mL) was refluxed for 2 h. The reaction mixture was poured into 1 M NaOH aqueous solution and extracted with AcOEt. The extract was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was washed with hexane/AcOEt (1/1) and recrystallized from MeOH to give the title compound (294 mg).

Workup

  1. temperaturewas refluxed for 2 h
  2. extractionextracted with AcOEt
  3. washThe extract was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. washThe residue was washed with hexane/AcOEt (1/1)
  7. customrecrystallized from MeOH

Sources & evidence

ORD record
ord-9a529bc796084ec299f14e48d4562dc6
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

Loading…