p-Toluenesulfonic acid monohydrate → 1-[5-[(Z)-2-cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-thiophen-2-yl]-piperidin-4-yl diethylamino-acetate p-toluenesulfonate

HRID 2366440

Reaktionsgleichung

Reaktionsgleichung von HRID 2366440
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[C:11](=[CH:14]/[C:15]2[S:16][C:17]([N:20]3[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22][CH2:21]3)=[CH:18][CH:19]=2)/[C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[Na+].[CH2:28]([N:30]([CH2:35][CH3:36])[CH2:31][C:32]([O-])=[O:33])[CH3:29].O.[C:38]1([CH3:48])[CH:43]=[CH:42][C:41]([S:44]([OH:47])(=[O:46])=[O:45])=[CH:40][CH:39]=1>C1(C)C=CC=CC=1>[C:38]1([CH3:48])[CH:39]=[CH:40][C:41]([S:44]([OH:47])(=[O:45])=[O:46])=[CH:42][CH:43]=1.[CH2:28]([N:30]([CH2:31][C:32]([O:26][CH:23]1[CH2:22][CH2:21][N:20]([C:17]2[S:16][C:15](/[CH:14]=[C:11](\[C:12]#[N:13])/[C:5]3[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)=[CH:19][CH:18]=2)[CH2:25][CH2:24]1)=[O:33])[CH2:35][CH3:36])[CH3:29]

Komponenten

5

Edukt 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 16757522(Z)-2-(3,4-dimethoxyphenyl)-3-(5-(4-hydroxypiperidin-1-yl)thiophen-2-yl)acrylonitrileHCID 23670834Glycine, N,N-diethyl-, sodium salt (1:1)

Produkt 1

HCID 119647871-[5-[(Z)-2-cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-thiophen-2-yl]-piperidin-4-yl diethylamino-acetate p-toluenesulfonateAusbeute 37,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Compound 6 (480 mg) was dissolved in toluene (100 mL), and N,N-diethylglycin sodium salt (296 mg) and p-toluenesulfonic acid monohydrate (490 mg) were added to the solution, followed by stirring under reflux for 5 hours. The solvent was evaporated to dryness, and the residue was purified by silica gel column chromatography (CHCl3-MeOH), to thereby yield the target product (yield: 237 mg, 37.7%).

Aufarbeitung

  1. temperatureunder reflux for 5 hours
  2. customThe solvent was evaporated to dryness
  3. customthe residue was purified by silica gel column chromatography (CHCl3-MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-34166a4ba0b14e9ea5e855b7b0ac7241
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697742B2

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