Tetrahydrofuran → HCID 117660506, compound

HRID 1428401Notes

Reaction equation

HRID 1428401 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]1[N:15]([CH2:16]C(OCC)=O)[C:14]2[CH:22]=[C:23]([Cl:27])[C:24]([Cl:26])=[CH:25][C:13]=2[N:12]=1)[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:28]1[CH2:32][O:31]CC1.[CH3:33][Mg]Br>O>[Cl:26][C:24]1[C:23]([Cl:27])=[CH:22][C:14]2[N:15]([CH2:16][C:32]([OH:31])([CH3:28])[CH3:33])[C:11]([CH2:10][N:8]([CH3:9])[C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[N:12][C:13]=2[CH:25]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 117662400HCID 117662400, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 117660506HCID 117660506, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of ethyl (2-{[(tert-butoxycarbonyl)(methyl)amino]methyl}-5,6-dichloro-1H-benzimidazol-1-yl)acetate (390 mg) and THF (8 mL) was added dropwise methylmagnesium bromide (3 M THF solution, 0.94 mL) at room temperature, followed by stirring at room temperature for 1 hour. To the reaction mixture was added water, followed by extraction with EtOAc. The organic layer was washed with brine, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: Hex/EtOAc=70/30-40/60) to obtain tert-butyl {[5,6-dichloro-1-(2-hydroxy-2-methylpropyl)-1H-benzimidazol-2-yl]methyl}methylcarbamate (70 mg).

Workup

  1. extractionfollowed by extraction with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: Hex/EtOAc=70/30-40/60)

Sources & evidence

ORD record
ord-0044cb81eae74dec82381f294e475006
Source dataset
uspto-grants-2015_01
Patent number
US08937087B2

Reaction notes

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