2-Imidazolidinone → HCID 53492514, compound

HRID 1800915Notes

Reaction equation

HRID 1800915 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]2[C:17]([CH3:19])([CH3:18])[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:20]([OH:22])=[O:21])[CH:14]=3)[NH:9]2)[CH:5]=[CH:6][CH:7]=1.[NH:23]1[CH2:27][CH2:26][NH:25][C:24]1=[O:28].Cl.CN(C)CC(O)=O.C(=O)([O-])[O-].[K+].[K+].I[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>CS(C)=O.[Cu]I>[CH3:18][C:17]1([CH3:19])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:20]([OH:22])=[O:21])[CH:14]=2)[NH:9][CH:8]1[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([N:23]2[CH2:27][CH2:26][N:25]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:24]2=[O:28])[CH:3]=1

Participants

8

Reactant 5

HCID 84532-ImidazolidinoneHCID 11430Potassium Carbonate2×HCID 11575IodobenzeneHCID 75605N,N-Dimethylglycine hydrochloride2×HCID 584761942-(3-Bromophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

Product 1

HCID 53492514HCID 53492514, compoundYield 9.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst2×HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-(3-bromo-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (720 mg, 2 mmol), imidazolidin-2-one (861 mg, 10 mmol), copper(I) iodide (229 mg, 1.2 mmol), N,N-dimethylglycine hydrochloride (224 g, 1.6 mmol) and potassium carbonate (829 mg, 6 mmol) in dimethyl sulfoxide (5 mL) was stirred at 120° C. for 12 h. Then the reaction mixture cooled to room temperature. Iodo-benzene (2.17 mL, 20 mmol), copper(I) iodide (229 mg, 1.2 mmol), N,N-dimethylglycine hydrochloride (224 g, 1.6 mmol) and potassium carbonate (829 mg, 6 mmol) was added. The reaction mixture was stirred at 120° C. for 12 h. Then the reaction mixture cooled to room temperature. The reaction mixture was extracted with ethyl acetate (2×200 mL), washed with water (2×50 mL) and saturated aqueous ammonium chloride solution (2×50 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% formic acid in water) afforded 3,3-dimethyl-2-[3-(2-oxo-3-phenyl-imidazolidin-1-yl)-phenyl]-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (82 mg, 9%) as a white solid: LC/MS m/e calcd for C27H27N3O3 (M+H)+: 442.53, observed: 442.1.

Workup

  1. temperatureThen the reaction mixture cooled to room temperature
  2. stirringThe reaction mixture was stirred at 120° C. for 12 h
  3. temperatureThen the reaction mixture cooled to room temperature
  4. extractionThe reaction mixture was extracted with ethyl acetate (2×200 mL)
  5. washwashed with water (2×50 mL) and saturated aqueous ammonium chloride solution (2×50 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. 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% formic acid in water)

Sources & evidence

ORD record
ord-81f952b56c534c42b29d81bcffaf05b0
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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