Water → 5-{1-[N-(3-trifluoromethylphenyl)amino]carbonylmethyl-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl}thiazolidine-2,4-dione

HRID 504041Notes

Reaction equation

HRID 504041 reaction equation
[C:1]([CH2:4][N:5]1[C:14]2[C:9](=[C:10]([CH2:17][CH:18]3[S:22][C:21](=[O:23])[NH:20][C:19]3=[O:24])[CH:11]=[CH:12][C:13]=2[O:15][CH3:16])[CH2:8][CH2:7][C:6]1=[O:25])(O)=[O:2].[F:26][C:27]([F:36])([F:35])[C:28]1[CH:29]=[C:30]([CH:32]=[CH:33][CH:34]=1)[NH2:31].ON1C2C=CC=CC=2N=N1.O>CN(C=O)C>[F:26][C:27]([F:35])([F:36])[C:28]1[CH:29]=[C:30]([NH:31][C:1]([CH2:4][N:5]2[C:14]3[C:9](=[C:10]([CH2:17][CH:18]4[S:22][C:21](=[O:23])[NH:20][C:19]4=[O:24])[CH:11]=[CH:12][C:13]=3[O:15][CH3:16])[CH2:8][CH2:7][C:6]2=[O:25])=[O:2])[CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73753-(Trifluoromethyl)anilineHCID 757711-HydroxybenzotriazoleHCID 866139485-(1-Carboxymethyl-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl)thiazolidine-2,4-dione

Product 1

HCID 866139505-{1-[N-(3-trifluoromethylphenyl)amino]carbonylmethyl-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl}thiazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

500 mg of 5-(1-carboxymethyl-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl)thiazolidine-2,4-dione was dissolved in 5 ml of DMF. 0.35 ml of 3-trifluoromethyl aniline, 0.32 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride(WSC), and 0.25 g of 1-hydroxybenzotriazole (HOBT) were added to the solution, followed by stirring at room temperature overnight. Water was added to the reaction liquid, and the solid thus obtained was separated by filtration. The solid was dissolved in methylene chloride, washed with sodium chloride solution, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride:methanol=50:1), giving 412 mg of 5-{1-[N-(3-trifluoromethylphenyl)amino]carbonylmethyl-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl}thiazolidine-2,4-dione.

Workup

  1. customthe solid thus obtained
  2. customwas separated by filtration
  3. dissolutionThe solid was dissolved in methylene chloride
  4. washwashed with sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (methylene chloride:methanol=50:1)

Sources & evidence

ORD record
ord-8bdcfb92ad8b4ce0a598f4b4d98bf2b4
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

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