Propyl mercaptan → 6-Chloro-N-cyclohexyl-2-(propylthio)nicotinamide

To a solution of propane thiol (2.975 mL, 32.89 mmol)l in DMF (25 mL) was added slowly a solution of 1N NaHMDS in THF (33 ml, 33.00 mmol). The mixture was stirred for ten minutes at room temperature and then added slowly to a solution of 2,6-dichloro-N-cyclohexyl-pyridine-3-carboxamide (Intermediate 1, 8.95 g, 32.89 mmol) in DMF (50 mL). The reaction was stirred at room temperature for two hours. The reaction was stopped and most of the THF and DMF was evaporated. The product was extracted with DCM (150 mL), washed with water (2×25 ml) and brine (25 mL). The solution was dried over MgSO4 and evaporated under reduced pressure to give a slightly pink solid. The solid was triturated in hexane and filtered; all of the coloured impurity went into solution to leave a white solid (7.84 g, 76%).

1. stirringThe reaction was stirred at room temperature for two hours
2. customwas evaporated
3. extractionThe product was extracted with DCM (150 mL)
4. washwashed with water (2×25 ml) and brine (25 mL)
5. dry with materialThe solution was dried over MgSO4
6. customevaporated under reduced pressure
7. customto give a slightly pink solid
8. customThe solid was triturated in hexane
9. filtrationfiltered

ORD record

ord-0cbcc6461ac04fb5aedf8fddab84e898

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08673938B2