Methyl iodide → HCID 118023581, compound

HRID 929297Notes

Reaction equation

HRID 929297 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:8]([N:9]([CH2:18][CH3:19])[C:10](=[O:17])[CH2:11][CH:12]2[CH2:15][NH:14][C:13]2=[O:16])=[CH:7][N:6]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[N:5]=1.[CH3:26]I>CN(C=O)C>[Cl:3][C:4]1[C:8]([N:9]([CH2:18][CH3:19])[C:10](=[O:17])[CH2:11][CH:12]2[CH2:15][N:14]([CH3:26])[C:13]2=[O:16])=[CH:7][N:6]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[N:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 118023799HCID 118023799, compound

Product 1

HCID 118023581HCID 118023581, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of NaH (60% dispersion in oil, 0.029 g, 0.72 mmol) in DMF (2 mL) was added N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-2-(2- oxoazetidin-3-yl)acetamide (0.20 g, 0.60 mmol) in DMF (0.5 mL), dropwise, at a temperature of about −10° C. over one minute. The reaction mixture was charged with methyl iodide (0.093 g, 0.66 mmol) in DMF (0.5 mL), dropwise, and stirred for 5 minutes. The reaction mixture was quenched with ice water (10 mL) and extracted with EtOAc (3×15 mL). The organic layers were combined and washed with water (3×10 mL) and brine (10 mL), dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by flash chromatography eluting with 1%-8% MeOH/CH2Cl2 to afford the title compound F32 as a gum (0.065 g, 31%).

Workup

  1. customThe reaction mixture was quenched with ice water (10 mL)
  2. extractionextracted with EtOAc (3×15 mL)
  3. washwashed with water (3×10 mL) and brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography
  7. washeluting with 1%-8% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-4f8cdca22cf244b8a34d7f43bd0365d3
Source dataset
uspto-grants-2016_03
Patent number
US09295260B2

Reaction notes

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