Propyl mercaptan → Methyl 4-[4-(cyclohexylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoate

Propane thiol (88 mg, 1.16 mmol) was dissolved in DMF (5 mL) and treated at ambient temperature with a 1M solution of NaHMDS in THF (1.16 mL). After stirring for 15 min the clear solution was added to a suspension of methyl 4-[5-chloro-4-(cyclohexylcarbamoyl)pyrazol-1-yl]benzoate (Intermediate #15) (378 mg, 1.05 mmol) in DMF (10 mL). Stirring was continued at ambient temperature for 2 h and then the reaction mixture was diluted with ethyl acetate (100 mL), washed with water (4×25 mL) and dried (MgSO4). Volatiles were removed by evaporation under reduced pressure to give a clear oil which was purified by chromatography on silica gel, eluting with an ethyl acetate/hexane gradient (0-50%) to give the title compound as a white solid. (363 mg, 86%)

1. stirringStirring
2. waitwas continued at ambient temperature for 2 h
3. washwashed with water (4×25 mL)
4. dry with materialdried (MgSO4)
5. customVolatiles were removed by evaporation under reduced pressure
6. customto give a clear oil which
7. customwas purified by chromatography on silica gel
8. washeluting with an ethyl acetate/hexane gradient (0-50%)

ORD-Eintrag

ord-a7bc87b88a7f425faeacc8fb5aef976d

Quelldatensatz

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08344016B2