2-Naphthoic acid → 5-{8-Methoxy-1-[4-(2-naphthoylamino)benzyl]-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl}thiazolidin-2,4-dione

HRID 504030Notes

Reaction equation

HRID 504030 reaction equation
C(N(CC)CC)C.C(OP(C#N)(=O)OCC)C.[NH2:18][C:19]1[CH:46]=[CH:45][C:22]([CH2:23][N:24]2[C:33]3[C:28](=[C:29]([CH2:36][CH:37]4[S:41][C:40](=[O:42])[NH:39][C:38]4=[O:43])[CH:30]=[CH:31][C:32]=3[O:34][CH3:35])[CH2:27][CH2:26][C:25]2=[O:44])=[CH:21][CH:20]=1.[CH:47]1[C:56]2[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=2)[CH:50]=[CH:49][C:48]=1[C:57](O)=[O:58]>C(OCC)(=O)C.O.CN(C=O)C>[CH3:35][O:34][C:32]1[CH:31]=[CH:30][C:29]([CH2:36][CH:37]2[S:41][C:40](=[O:42])[NH:39][C:38]2=[O:43])=[C:28]2[C:33]=1[N:24]([CH2:23][C:22]1[CH:21]=[CH:20][C:19]([NH:18][C:57]([C:48]3[CH:49]=[CH:50][C:51]4[C:56](=[CH:55][CH:54]=[CH:53][CH:52]=4)[CH:47]=3)=[O:58])=[CH:46][CH:45]=1)[C:25](=[O:44])[CH2:26][CH2:27]2

Participants

8

Reactant 4

HCID 71232-Naphthoic acidHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 866139395-[1-(4-Aminobenzyl)-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione

Product 1

HCID 866139405-{8-Methoxy-1-[4-(2-naphthoylamino)benzyl]-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl}thiazolidin-2,4-dioneYield 77%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.52 g of triethylamine and 0.42 g of diethylphosphoro cyanidate (DEPC) were added with ice cooling to a DMF solution (14 ml) of 0.7 g of 5-[1-(4-aminobenzyl)-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione and 0.59 g of 2-naphthoic acid, followed by stirring for 16 hours. Water and ethyl acetate were added to the reaction liquid, and the insoluble matter thus formed was collected by filtration. The collected insoluble matter was dissolved in a dichloromethane-methanol mixed solvent and concentrated. The residue was washed with diethylether and diisopropyl ether. The residue was dried under reduced pressure, giving 0.74 g (77% yield) of 5-{8-methoxy-1-[4-(2-naphthoylamino)benzyl]-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl}thiazolidin-2,4-dione as a white amorphous solid.

Workup

  1. customthe insoluble matter thus formed
  2. filtrationwas collected by filtration
  3. dissolutionThe collected insoluble matter was dissolved in a dichloromethane-methanol mixed solvent
  4. concentrationconcentrated
  5. washThe residue was washed with diethylether and diisopropyl ether
  6. customThe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-95b4d5be0b254e9eb339f63bacf5173a
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

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