N,N'-Dimethylethylenediamine → HCID 70497117, compound

HRID 2408021Notes

Reaction equation

HRID 2408021 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH3:23])=[C:6]([CH:8]2[CH2:17][C:16]([CH3:19])([CH3:18])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:20]([OH:22])=[O:21])[CH:14]=3)[NH:9]2)[CH:7]=1.[O:24]1[CH2:28][CH2:27][NH:26][C:25]1=[O:29].CNCCNC.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.[Cu]I>[CH3:18][C:16]1([CH3:19])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:20]([OH:22])=[O:21])[CH:14]=2)[NH:9][CH:8]([C:6]2[CH:7]=[C:2]([N:26]3[CH2:27][CH2:28][O:24][C:25]3=[O:29])[CH:3]=[CH:4][C:5]=2[CH3:23])[CH2:17]1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 739492-OxazolidinoneHCID 70495991HCID 70495991, compound

Product 1

HCID 70497117HCID 70497117, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture solution of 2-(5-bromo-2-methyl-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (1.36 g, 3.64 mmol), oxazolidin-2-one (330 mg, 3.82 mmol), copper(I) iodide (139 mg, 0.73 mmol), N,N′-dimethyl-ethane-1,2-diamine (0.157 mL, 1.46 mmol), and potassium carbonate (1.51 g, 10.9 mmol) in acetonitrile (25 mL) was stirred at 90° C. for 72 h. Then the reaction mixture was cooled to room temperature. The reaction mixture was extracted with ethyl acetate (200 mL×2), washed with saturated aqueous ammonium chloride solution (50 mL×3) and brine (50 mL×2), dried over anhydrous sodium sulfate and then concentrated in vacuo and the residue was purified by ISCO combi-flash chromatography (gradient elution, 30-50% ethyl acetate in petroleum ether) to afford 4,4-dimethyl-2-[2-methyl-5-(2-oxo-oxazolidin-3-yl)-phenyl]-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (0.4 g, 29%) as a white solid: MS (ESI) M+1=381.1.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (200 mL×2)
  2. washwashed with saturated aqueous ammonium chloride solution (50 mL×3) and brine (50 mL×2)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customthe residue was purified by ISCO combi-flash chromatography (gradient elution, 30-50% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-5b4830bc35f34b168fd13ada46a30995
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Reaction notes

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