HCID 117601197, compound → HCID 117602002, compound

HRID 1773748Notes

Reaction equation

HRID 1773748 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([C:17]([O:19]C)=O)[C:10]3[NH:14][C:13](=[O:15])[NH:12][C:11]=3[CH:16]=2)=[C:5]([CH3:21])[O:4][N:3]=1.[CH:22]([Mg]Br)([CH3:24])[CH3:23]>C1COCC1>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([C:17](=[O:19])[CH:22]([CH3:24])[CH3:23])[C:10]3[NH:14][C:13](=[O:15])[NH:12][C:11]=3[CH:16]=2)=[C:5]([CH3:21])[O:4][N:3]=1

Participants

4

Reactant 2

HCID 117601197HCID 117601197, compoundHCID 178418365HCID 178418365, compound

Product 1

HCID 117602002HCID 117602002, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 6-(3,5-dimethylisoxazol-4-yl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-4-carboxylate (100 mg, 0.35 mmol) was dissolved in 5 mL of THF and stirred at room temperature followed by the addition of isopropylmagnesium bromide (0.87 mL, 2.0 mmol). Addition Grignard was added in 1 hour intervals until the starting material was consumed. Once complete, the crude reaction mixture was quenched with DI water and extracted 3× with ethyl acetate. Combined organic layers were washed with brine, dried over sodium sulphate, filtered, concentrated in vacuo, and purified via HPLC.

Workup

  1. additionAddition Grignard
  2. additionwas added in 1 hour intervals until the starting material
  3. customwas consumed
  4. customOnce complete, the crude reaction mixture
  5. customwas quenched with DI water
  6. extractionextracted 3× with ethyl acetate
  7. washCombined organic layers were washed with brine
  8. dry with materialdried over sodium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. custompurified via HPLC

Sources & evidence

ORD record
ord-a8df114929634879bdd3c65ea1c83ebf
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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