Sodium methanethiolate → 3,4-Dichloro-5-methyl-N-{1-[2-(methylthio)pyrimidin-4-yl]piperidin-4-yl}-1H-pyrrole-2-carboxamide
Reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:23]=[CH:22][N:21]=[C:20](Cl)[N:19]=2)[CH2:14][CH2:13]1)=[O:10].[CH3:25][S-:26].[Na+]>CN(C=O)C.CCOC(C)=O.O>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([S:26][CH3:25])[N:19]=2)[CH2:14][CH2:13]1)=[O:10]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 90 °C
Procedure
3,4-Dichloro-N-[1-(2-chloropyrimidin-4-yl)piperidin-4-yl]-5-methyl-1H-pyrrole-2-carboxamide (Example 307, 200 mg, 0.515 mmol) and sodium thiomethoxide (108.2 mg, 1.545 mmol) were combined in DMF (12 ml) and heated at 90° C. for 1 h. The reaction mixture was cooled to room temperature, diluted with EtOAc and water. The phases were separated, and the aqueous phase was extracted three times with EtOAc. The combined organic portions were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give a peach coloured solid (200 mg, 0.499 mmol, 97% yield) that was used without further purification.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- customThe phases were separated
- extractionthe aqueous phase was extracted three times with EtOAc
- washThe combined organic portions were washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-1ef28c3748404045a8c39f011a2461df
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07709503B2
Reaction notes
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