N,N'-Dimethylethylenediamine → HCID 70496923, compound

HRID 2408100Notes

Reaction equation

HRID 2408100 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([Cl:24])[CH:8]=[C:9]2[C:14]=1[NH:13][CH:12]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17](Br)[CH:16]=1)[CH2:11][C:10]2([CH3:23])[CH3:22])=[O:4].[O:25]1[CH2:29][CH2:28][NH:27][C:26]1=[O:30].CNCCNC.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu]I>[Cl:24][C:7]1[CH:8]=[C:9]2[C:14](=[C:5]([C:3]([OH:2])=[O:4])[CH:6]=1)[NH:13][CH:12]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N:27]3[CH2:28][CH2:29][O:25][C:26]3=[O:30])[CH:16]=1)[CH2:11][C:10]2([CH3:23])[CH3:22]

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 739492-OxazolidinoneHCID 67291316HCID 67291316, compound

Product 1

HCID 70496923HCID 70496923, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-(3-bromo-phenyl)-6-chloro-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester (1 g, 2.5 mmol), oxazolidin-2-one (230 mg, 2.63 mmol), copper(I) iodide (95 mg, 0.5 mmol), N,N′-dimethyl-ethane-1,2-diamine (0.11 mL, 1 mmol), and potassium carbonate (1.04 g, 7.5 mmol) in dimethyl sulfoxide (10 mL). The reaction mixture was stirred at 120° C. for 16 h. Then the reaction mixture cooled to room temperature. The reaction mixture was extracted with ethyl acetate (2×50 mL), washed with water (2×20 mL) and saturated aqueous ammonium chloride solution (2×20 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded 6-chloro-4,4-dimethyl-2-[3-(2-oxo-oxazolidin-3-yl)-phenyl]-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid (0.8 g, 80%) as a white solid: MS (ESI) M+1=400.1.

Workup

  1. temperatureThen the reaction mixture cooled to room temperature
  2. extractionThe reaction mixture was extracted with ethyl acetate (2×50 mL)
  3. washwashed with water (2×20 mL) and saturated aqueous ammonium chloride solution (2×20 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water)

Sources & evidence

ORD record
ord-2dd0fce4c1d6417f8e9e7e0adb80757b
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Reaction notes

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