Hexane → 2-pyridin-2-yl-N-[2-[2-[[3-(trifluoromethyl)phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]acetamide
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([O:10]C)=O.[F:12][C:13]([F:34])([F:33])[C:14]1[CH:15]=[C:16]([S:20]([CH2:23][CH2:24][S:25][C:26]2[C:31]([NH2:32])=[CH:30][CH:29]=[CH:28][N:27]=2)(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=1.CCCCCC>C1(C)C(C)=CC=CC=1.CCOC(C)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([NH:32][C:31]1[C:26]([S:25][CH2:24][CH2:23][S:20]([C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([C:13]([F:33])([F:34])[F:12])[CH:15]=2)(=[O:22])=[O:21])=[N:27][CH:28]=[CH:29][CH:30]=1)=[O:10]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 150 °C
Procedure
302 mg (2.0 mmol) methyl 2-(pyridin-2-yl)acetate were added to a solution of 362 mg (1.0 mmol) [2-[2-[[3-(trifluoromethyl)phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]amine (VPF-001) in xylene (4 ml) and the mixture was then heated for 7 h at 150° C. After cooling to RT the mixture was diluted with EtOAc and the phases were separated. The organic phase was washed with water and brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. Column chromatography (hexane/EE 6:4) of the residue yielded 154 mg (0.32 mmol, 32%) 2-pyridin-2-yl-N-[2-[2-[[3-(trifluoromethyl)phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]acetamide. MS: m/z 482.1 [M+H]+.
Workup
- temperatureAfter cooling to RT the mixture
- customthe phases were separated
- washThe organic phase was washed with water and brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated to small volume under vacuum
Sources & evidence
- ORD record
- ord-b78a0ef78d5f4af2a2588c7d220d1fc4
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08247573B2
Reaction notes
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