4-Isopropylaniline → 5-{1-[4-(4-Isopropylphenylaminocarbonyl)benzyl]-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl}thiazolidine-2,4-dione

HRID 1811444Notes

Reaction equation

HRID 1811444 reaction equation
C(N(CC)CC)C.P(C#N)(=O)(OCC)OCC.[CH3:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:41][CH:42]2[S:46][C:45](=[O:47])[NH:44][C:43]2=[O:48])=[C:24]2[C:29]=1[N:28]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([C:37](O)=[O:38])=[CH:33][CH:32]=1)[C:27](=[O:40])[CH2:26][CH2:25]2.[CH:49]([C:52]1[CH:58]=[CH:57][C:55]([NH2:56])=[CH:54][CH:53]=1)([CH3:51])[CH3:50]>O.CN(C=O)C>[CH:49]([C:52]1[CH:58]=[CH:57][C:55]([NH:56][C:37]([C:34]2[CH:33]=[CH:32][C:31]([CH2:30][N:28]3[C:29]4[C:24](=[C:23]([CH2:41][CH:42]5[S:46][C:45](=[O:47])[NH:44][C:43]5=[O:48])[CH:22]=[CH:21][C:20]=4[O:19][CH3:18])[CH2:25][CH2:26][C:27]3=[O:40])=[CH:36][CH:35]=2)=[O:38])=[CH:54][CH:53]=1)([CH3:51])[CH3:50]

Participants

7

Reactant 4

HCID 74644-IsopropylanilineHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 866139425-[8-Methoxy-1-(4-carboxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione

Product 1

HCID 866139435-{1-[4-(4-Isopropylphenylaminocarbonyl)benzyl]-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl}thiazolidine-2,4-dioneYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

0.34 g of triethylamine and 0.28 g of diethyl phosphorocyanidate (DEPC) were added with ice cooling to a DMF solution (10 ml) of 0.5 g of 5-[8-methoxy-1-(4-carboxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione and 0.23 g of 4-isopropylaniline, followed by stirring for 0.5 hours. Water was added to the reaction liquid and the mixture was extracted with ethyl acetate. The organic layer was washed twice with water and once with saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled off under a reduced pressure, the residue was purified by silica gel column chromatography (dichloromethane:methanol=100:1→20:1), and recrystallized from a mixed solvent of ethyl acetate and n-hexane, giving 0.57 g (64% yield) of 5-{1-[4-(4-isopropylphenylaminocarbonyl)benzyl]-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl}thiazolidine-2,4-dione as a white powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed twice with water and once with saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under a reduced pressure
  5. customthe residue was purified by silica gel column chromatography (dichloromethane:methanol=100:1→20:1)
  6. customrecrystallized from a mixed solvent of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-c0ba03f473c549d296016c1d27a3a0b8
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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