Pyridine → 3-(2-Cyclohexyl-6-oxo-piperidin-1-yl)-5-phenyl-thiophene-2-carboxylic acid methyl ester

HRID 579192

Reaktionsgleichung

Reaktionsgleichung von HRID 579192
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:8][C:9]=1[NH:10][CH:11]([CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[CH2:12][CH2:13][CH2:14][C:15]([OH:17])=O)=[O:4].N1C=CC=CC=1.CC(OC(OC(OC(C)(C)C)=O)=O)(C)C>O1CCCCO1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[CH:8][C:9]=1[N:10]1[C:15](=[O:17])[CH2:14][CH2:13][CH2:12][CH:11]1[CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1)=[O:4]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 90495Di-tert-butyl dicarbonateHCID 666848323-(4-Carboxy-1-cyclohexyl-butylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester

Produkt 1

HCID 666839463-(2-Cyclohexyl-6-oxo-piperidin-1-yl)-5-phenyl-thiophene-2-carboxylic acid methyl esterAusbeute 39,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1385701,2-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a vial containing a solution of 3-(4-Carboxy-1-cyclohexyl-butylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester (40 mg, 0.096 mmol, 1.0 equiv) in 1,2-dioxane (1.0 mL) was added pyridine (3.8 mg, 0.048 mmol, 0.5 equiv) and Boc2O (25 mg, 0.166 mmol, 1.2 equiv). The vial was then sealed and heated at 65° C. for 18 hours. The solution was concentrated and the residue was purified by silica gel column chromatography, EtOAc/Heptane 5% to 100% to give product 15 mg (yield 39%).

Aufarbeitung

  1. customThe vial was then sealed
  2. concentrationThe solution was concentrated
  3. customthe residue was purified by silica gel column chromatography, EtOAc/Heptane 5% to 100%

Quellen und Nachweise

ORD-Eintrag
ord-d51df7bce6ca4f8bad3f9a5ca5bb7f2e
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040690B2

Verknüpfte Notizen

Wird geladen…