N-[(4-cyano-3-fluoro-phenyl)-(3-methyl-3H-imidazol-4-yl)-methylene]-2-methylpropanesulfinamide → N-[1-(4-cyano-3-fluoro-phenyl)-1-(3-methyl-3H-imidazol-4-yl)-ethyl]-2-methylpropanesulfinamide

HRID 413419Notes

Reaction equation

HRID 413419 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:17]2[N:18]([CH3:22])[CH:19]=[N:20][CH:21]=2)=[N:10][S:11]([CH2:13][CH:14]([CH3:16])[CH3:15])=[O:12])=[CH:5][C:4]=1[F:23])#[N:2].[CH3:24][Mg+].[Br-]>C1COCC1.CCOCC>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:10][S:11]([CH2:13][CH:14]([CH3:16])[CH3:15])=[O:12])([C:17]2[N:18]([CH3:22])[CH:19]=[N:20][CH:21]=2)[CH3:24])=[CH:5][C:4]=1[F:23])#[N:2]

Participants

5

Reactant 2

HCID 86584782N-[(4-cyano-3-fluoro-phenyl)-(3-methyl-3H-imidazol-4-yl)-methylene]-2-methylpropanesulfinamideHCID 178418689HCID 178418689, compound

Product 1

HCID 18533209N-[1-(4-cyano-3-fluoro-phenyl)-1-(3-methyl-3H-imidazol-4-yl)-ethyl]-2-methylpropanesulfinamide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-[(4-Cyano-3-fluoro-phenyl)-(3-methyl-3H-imidazol-4-yl)-methylene]-2-methylpropanesulfinamide (1.50 g, 4.51 mmol) was dissolved in anhydrous THF (30 mL) at 0° C. and treated with a 3.0M solution of MeMgBr (4.50 mL, 13.5 mmol) in Et2O. After 15 min the reaction was quenched with aq. NH4Cl solution, diluted with saturated NaHCO3 solution and extracted with CH2Cl2 (3×). The combined organic layers were dried (MgSO4), filtered, concentrated, and recrystallized from 95% EtOAc/Hexane to give the title compound.

Workup

  1. customAfter 15 min the reaction was quenched with aq. NH4Cl solution
  2. additiondiluted with saturated NaHCO3 solution
  3. extractionextracted with CH2Cl2 (3×)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customrecrystallized from 95% EtOAc/Hexane

Sources & evidence

ORD record
ord-c4951cdf9ea64dc4ad51c9d7d3c64a88
Source dataset
uspto-grants-2003_05
Patent number
US06566385B2

Reaction notes

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