Oxalyl chloride → HCID 89498529, compound

HRID 588662Notes

Reaction equation

HRID 588662 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=O)C.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

Conditions

Temperature
0 °C

Procedure

To a solution of EXAMPLE 23C (7.89 g) in DMF (80 mL) and pyridine (5 mL) at 0° C. was added dropwise oxalyl chloride (5.52 mL). The mixture was stirred at 0° C. for 30 minutes and ice-water was added to quench the reaction. The resulting mixture was diluted with ethyl acetate and washed with aqueous NaHCO3 and water extensively. The organic layer was dried over Na2SO4, filtered, and concentrated. The residue was purified by flash column, eluting with dichloromethane to provide the title compound.

Workup

  1. customto quench
  2. customthe reaction
  3. washwashed with aqueous NaHCO3 and water extensively
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash column
  8. washeluting with dichloromethane

Sources & evidence

ORD record
ord-cc483ffe34c84f489478107316fc567f
Source dataset
uspto-grants-2016_01
Patent number
US09227963B2

Reaction notes

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