Tetrahydrofuran → HCID 89702430, compound

HRID 2203034Notes

Reaction equation

HRID 2203034 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[Cl:5][C:6]1[CH:37]=[CH:36][C:9]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][N:15]([C:18]3[CH:19]=[CH:20][C:21]4[N:25]=[C:24]([CH:26]5[CH2:28][CH:27]5[C:29]([O:31]C)=O)[N:23]([CH3:33])[C:22]=4[CH:34]=3)[C:14](=[O:35])[CH:13]=2)=[CH:8][CH:7]=1.[CH2:38]1COC[CH2:39]1>>[Cl:5][C:6]1[CH:37]=[CH:36][C:9]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][N:15]([C:18]3[CH:19]=[CH:20][C:21]4[N:25]=[C:24]([CH:26]5[CH2:28][CH:27]5[C:29]([OH:31])([CH2:1][CH3:2])[CH2:38][CH3:39])[N:23]([CH3:33])[C:22]=4[CH:34]=3)[C:14](=[O:35])[CH:13]=2)=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 121386252HCID 121386252, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 89702430HCID 89702430, compound

Procedure

Ethylmagnesium bromide (1.0 M solution in THF, 1.29 ml) was added to a solution of methyl(1RS,2RS)-2-(6-(4-((4-chlorobenzyl)oxy)-2-oxopyridin-1(2H)-yl)-1-methyl-1H-benzimidazol-2-yl)cyclopropanecarboxylate (150 mg) in THF (5 ml) at 0° C., and the mixture was stirred at room temperature for 3 h. The mixture was quenched with saturated NH4Cl solution, and extracted with EtOAc. The organic layer was separated, washed with water and brine successively, dried over MgSO4, and concentrated in vacuo. The residue was purified by NH silica gel column chromatography (EtOAc/MeOH), and the resulting solid was crystallized from EtOH to give the title compound (48 mg) as a white solid.

Workup

  1. customThe mixture was quenched with saturated NH4Cl solution
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with water and brine successively
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by NH silica gel column chromatography (EtOAc/MeOH)
  8. customthe resulting solid was crystallized from EtOH

Sources & evidence

ORD record
ord-3ea1d5e17fa64f3eb15be9d043a97c40
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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