Hydrochloric Acid → HCID 89691132, compound

HRID 2203046Notes

Reaction equation

HRID 2203046 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH:10]3[CH2:13][C:12](=[CH:14][O:15]C)[CH2:11]3)[NH:7][C:6]=2[CH:17]=1.Cl.[CH3:19]C#N>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH:10]3[CH2:13][CH:12]([CH:14]=[O:15])[CH2:11]3)[N:7]([CH3:19])[C:6]=2[CH:17]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 89690325HCID 89690325, compound

Product 1

HCID 89691132HCID 89691132, compound

Procedure

To a solution of 6-bromo-2-(3-(methoxymethylidene)cyclobutyl)-1H-benzimidazole (850 mg) in CH3CN (20 ml) was added 2 M HCl (4.2 ml), and the resulting mixture was stirred at same temperature for 16 h. The reaction mixture was then quenched with saturated NaHCO3 solution, and extracted with DCM. The extract was washed with brine, dried over Na2SO4, concentrated in vacuo and purified by column chromatography (hexane/EtOAc) to afford two isomers of the title compound (Less polar isomer: 200 mg, polar isomer: 300 mg) as yellow sticky solids.

Workup

  1. customThe reaction mixture was then quenched with saturated NaHCO3 solution
  2. extractionextracted with DCM
  3. washThe extract was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-16cbb2bd38684e2c83d9d7f63f7e4eca
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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