N,N'-Dimethylethylenediamine → HCID 10911100, compound

HRID 1364874Notes

Reaction equation

HRID 1364874 reaction equation
I[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[C:12](=[O:15])([O-])[O-:13].[K+].[K+].C[NH:19][CH2:20][CH2:21]NC>C1(C)C=CC=CC=1.C(OCC)(=O)C.[Cu](I)I>[O:15]=[C:12]1[N:19]([C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=2)[CH2:20][CH2:21][O:13]1

Participants

7

Reactant 3

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 69273Methyl 4-iodobenzoate

Product 1

HCID 10911100HCID 10911100, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 1 g of methyl 4-iodobenzoate, 399 mg of 2-oxozolidone, 1.1 g of potassium carbonate, 34 mg of N,N′-dimethylethylenediamine and 73 mg of copper iodide in 10 mL of toluene was heated to 150° C. in a sealed microwave reactor for 2 h. The reaction mixture was diluted with ethyl acetate, washed with H2O, dried (MgSO4) and evaporated. Purified by silica gel chromatography (20-70% ethyl acetate/hexane) to afford methyl 4-(2-oxooxazolidin-3-yl)benzoate. 530 mg of methyl 4-(2-oxooxazolidin-3-yl)benzoate was hydrolyzed via Procedure M to give 4-(2-oxooxazolidin-3-yl)benzoic acid. 70 mg of 4-chloro-3-(pyridin-2-yl)aniline was coupled to 4-(2-oxooxazolidin-3-yl)benzoic acid via Procedure G. The product was purified on reverse phase HPLC to yield N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(2-oxooxazolidin-3-yl)benzamide. MS (Q1) 394.2 (M)+.

Workup

  1. washwashed with H2O
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customPurified by silica gel chromatography (20-70% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-898a21f50f8341c3b25008609b9fd999
Source dataset
uspto-grants-2011_02
Patent number
US07888364B2

Reaction notes

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