2-Phenylethanethiol → 6-chloro-N-cyclohexyl-2-phenethylsulfanyl-pyridine-3-carboxamide
Reaction equation
[C:1]1([CH2:7][CH2:8][SH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Cl[C:21]1[C:26]([C:27]([NH:29][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)=[O:28])=[CH:25][CH:24]=[C:23]([Cl:36])[N:22]=1>CN(C=O)C>[Cl:36][C:23]1[N:22]=[C:21]([S:9][CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:26]([C:27]([NH:29][CH:30]2[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]2)=[O:28])=[CH:25][CH:24]=1Participants
Procedure
To a solution of 2-phenylethanethiol (295 μl, 2.2 mmol) in DMF (3 ml) was added NaHMDS (2.2 ml, 2.2 mmol). The reaction was stirred at ambient temperature for 2 minutes then added to a solution of 2,6-dichloro-N-cyclohexyl-pyridine-3-carboxamide (Intermediate 1, 600 mg, 2.2 mmol) in DMF (2 ml). The reaction was stirred at ambient temperature for one hour. The solvent was evaporated under reduced pressure and the resulting residue was partitioned between citric acid (20 ml) and EtOAc (40 ml). The layers were separated and the organic layer was washed with sat NaHCO3 (20 ml), water (20 ml) and brine (10 ml), then dried (MgSO4), filtered and evaporated to a solid. This solid was triturated with EtOAc/IH (1:9) to yield the product as a white solid (700 mg, 85%).
Workup
- stirringThe reaction was stirred at ambient temperature for one hour
- customThe solvent was evaporated under reduced pressure
- customthe resulting residue was partitioned between citric acid (20 ml) and EtOAc (40 ml)
- customThe layers were separated
- washthe organic layer was washed with sat NaHCO3 (20 ml), water (20 ml) and brine (10 ml)
- dry with materialdried (MgSO4)
- filtrationfiltered
- customevaporated to a solid
- customThis solid was triturated with EtOAc/IH (1:9)
Sources & evidence
- ORD record
- ord-2593506c91d145a89e412e1be91a2307
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08673938B2
Reaction notes
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