Potassium Carbonate → N-[3-(benzyloxy)propyl]-6-chloro-N-cyclopentylpyridine-3-sulfonamide
Reaktionsgleichung
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:24][CH2:25][CH2:26][O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C=O)C.CCOC(C)=O>[CH2:28]([O:27][CH2:26][CH2:25][CH2:24][N:11]([CH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)[S:8]([C:5]1[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1Komponenten
6
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 40 °C
Versuchsvorschrift
A mixture of 1 g (3.84 mmol) of 6-chloro-N-cyclopentylpyridine-3-sulfonamide, 1.32 g (9.59 mmol) of K2CO3 and 0.88 mL (4.99 mmol) of [(3-bromopropoxy)methyl]benzene in 8 mL of anhydrous DMF is heated for 12 hours at 40° C. After cooling to room temperature, the medium is taken up in 300 mL of EtOAc, washed successively with water (2×100 mL), saturated NaHCO3 solution (100 mL) and brine (100 mL), dried over Na2SO4 and then concentrated under reduced pressure and purified by chromatography on a column of silica gel, eluting with a cyclohexane/EtOAc gradient of 0 to 10% EtOAc. 1.65 g of N-[3-(benzyloxy)propyl]-6-chloro-N-cyclopentylpyridine-3-sulfonamide are thus obtained in the form of an oil.
Aufarbeitung
- temperatureAfter cooling to room temperature
- washwashed successively with water (2×100 mL), saturated NaHCO3 solution (100 mL) and brine (100 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure
- custompurified by chromatography on a column of silica gel
- washeluting with a cyclohexane/EtOAc gradient of 0 to 10% EtOAc
Quellen und Nachweise
- ORD-Eintrag
- ord-79a85a28bdfb46ae98f3b4d96df4b87e
- Quelldatensatz
- uspto-grants-2013_09
- Patentnummer
- US08541455B2
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