Dimethylamine → HCID 73554652, compound

HRID 1261344Notes

Reaction equation

HRID 1261344 reaction equation
[Cl:1][C:2]1[C:3]2[CH:10]=[C:9]([C:11]([O-:13])=O)[N:8]([CH3:14])[C:4]=2[N:5]=[CH:6][N:7]=1.[Li+].C(Cl)(=O)C(Cl)=O.[CH3:22][N:23](C=O)[CH3:24].N(C)C>C(Cl)Cl.C1COCC1>[Cl:1][C:2]1[C:3]2[CH:10]=[C:9]([C:11]([N:23]([CH3:24])[CH3:22])=[O:13])[N:8]([CH3:14])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

7

Reactant 4

HCID 674DimethylamineHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 59424485HCID 59424485, compound

Product 1

HCID 73554652HCID 73554652, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A reaction mixture containing carboxylate 275 (78 mg, 0.36 mmo), oxalyl chloride (63 uL, 0.72 mmol), and a drop of DMF in DCM was stirred for 2 h. Solvents were removed under reduced pressure and the residue was re-dissolved in DCM (4 mL). To this solution Me2NH (360 μL, 0.72 mmol, 2M in THF) in THF was added and the mixture was stirred at room temperature for 4 h. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography (eluent EtOAc) to afford the title compound 276 (50 mg, 58% yield) as a yellowish solid. MS (m/z): 239.1(M+H) (found).

Workup

  1. customSolvents were removed under reduced pressure
  2. dissolutionthe residue was re-dissolved in DCM (4 mL)
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by flash column chromatography (eluent EtOAc)

Sources & evidence

ORD record
ord-9d43e9bc042d4e8aaec547157f49d2d3
Source dataset
uspto-grants-2013_06
Patent number
US08470850B2

Reaction notes

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