Oxalyl chloride → HCID 89498529, compound

HRID 1778918Notes

Reaction equation

HRID 1778918 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([C:8]([NH2:10])=O)[NH:5][C:6]=1[CH3:7].C(Cl)(=O)C(Cl)=O>CN(C)C=O.N1C=CC=CC=1.C(OCC)(=O)C>[I:1][C:2]1[CH:3]=[C:4]([C:8]#[N:10])[NH:5][C:6]=1[CH3:7]

Participants

6

Reactant 2

HCID 65578Oxalyl chlorideHCID 89498250HCID 89498250, compound

Product 1

HCID 89498529HCID 89498529, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of EXAMPLE 168C (300 mg) in N,N-dimethylformamide (6 mL) and pyridine (0.6 mL) at 0° C. was added dropwise oxalyl chloride (0.35 mL). The mixture was stirred at room temperature for 30 minutes, diluted with ethyl acetate and washed with saturated NaHCO3 and water extensively. The organic layer was dried over Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography, and eluted with dichloromethane to provide the title compound.

Workup

  1. washwashed with saturated NaHCO3 and water extensively
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. washeluted with dichloromethane

Sources & evidence

ORD record
ord-8fb784b07f7546f886ca9a9d1c25a5d2
Source dataset
uspto-grants-2016_02
Patent number
US09266877B2

Reaction notes

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