Piperidine → (E)-3-(3-{6-[1-methyl-1-(methylsulfonyl)ethyl]-8-quinolinyl}phenyl)-2-[4-(methylsulfonyl)phenyl]-2-propenoic acid

HRID 2187906Notes

Reaction equation

HRID 2187906 reaction equation
[CH3:1][C:2]([C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:18]3[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=3)[CH:21]=O)[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([S:4]([CH3:7])(=[O:6])=[O:5])[CH3:3].[CH3:26][S:27]([C:30]1[CH:35]=[CH:34][C:33]([CH2:36][C:37]([OH:39])=[O:38])=[CH:32][CH:31]=1)(=[O:29])=[O:28].N1CCCCC1.C(Cl)Cl.CCOC(C)=O.CC(O)=O>C1(C)C=CC=CC=1.C(Cl)Cl.CCOCC.C(Cl)Cl>[CH3:3][C:2]([C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:18]3[CH:19]=[C:20](/[CH:21]=[C:36](\[C:33]4[CH:32]=[CH:31][C:30]([S:27]([CH3:26])(=[O:28])=[O:29])=[CH:35][CH:34]=4)/[C:37]([OH:39])=[O:38])[CH:23]=[CH:24][CH:25]=3)[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([S:4]([CH3:7])(=[O:6])=[O:5])[CH3:1]

Participants

8

Reactant 4

HCID 8082PiperidineHCID 5723454-Mesylphenylacetic acidHCID 101550433-{6-[1-Methyl-1-(methylsulfonyl)ethyl]-8-quinolinyl}benzaldehydeHCID 21963926CH2Cl2 EtOAc AcOH

Product 1

HCID 22350086(E)-3-(3-{6-[1-methyl-1-(methylsulfonyl)ethyl]-8-quinolinyl}phenyl)-2-[4-(methylsulfonyl)phenyl]-2-propenoic acid

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 21881112Ethyl ether methylene chlorideSolvent

Procedure

A mixture of 3-{6-[1-methyl-1-(methylsulfonyl)ethyl]-8-quinolinyl}benzaldehyde from step 4 of Example 18 (2.33 g, 6.60 mmol), 4-(methylsulfonyl)phenyl acetic acid (1.71 g, 7.98 mmol) and piperidine (0.20 ml, 1.98 mmol) in 10 mL of toluene was refluxed for 2 days. The mixture was cooled to r.t., diluted with CH2Cl2, subjected to flash chromatography (CH2Cl2/EtOAc/AcOH, 50/50/1) and finally stirred with (Et2O/CH2Cl2) and isolated to give (E)-3-(3-{6-[1-methyl-1-(methylsulfonyl)ethyl]-8-quinolinyl}phenyl)-2-[4-(methylsulfonyl)phenyl]-2-propenoic acid (single isomer) as a white solid.

Workup

  1. temperaturewas refluxed for 2 days
  2. customisolated

Sources & evidence

ORD record
ord-78c99f7016d7483e8005b8a6cd5d2f52
Source dataset
uspto-grants-2002_06
Patent number
US06410563B1

Reaction notes

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