Reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH2:4][CH2:5][CH2:6][C:7](Cl)=[O:8].[F:11][C:12]1[CH:13]=[C:14]([C:22]2[S:26][C:25]([NH2:27])=[N:24][C:23]=2[CH3:28])[CH:15]=[CH:16][C:17]=1[S:18]([CH3:21])(=[O:20])=[O:19]>>[CH3:1][O:2][C:3](=[O:10])[CH2:4][CH2:5][CH2:6][C:7](=[O:8])[NH:27][C:25]1[S:26][C:22]([C:14]2[CH:15]=[CH:16][C:17]([S:18]([CH3:21])(=[O:19])=[O:20])=[C:12]([F:11])[CH:13]=2)=[C:23]([CH3:28])[N:24]=1Participants
3
Conditions
- Temperature
- 60 °C
Procedure
Methyl-4-(chloroformyl)butyrate (4.0 mmol) is added to a stirred solution of 5-(3-fluoro-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-ylamine (Example 72) (0.77 g, 2.69 mmol) and heated to 60° C. for 1.5 hours. The reaction mixture is allowed to cool to room temperature and the solvent removed in vacuo. The residue is washed with saturated sodium bicarbonate solution (2×50 ml) and water (1×50 ml). The product is extracted with ethyl acetate (2×50 ml) and the combined organic extracts dried (MgSO4). Removal of the solvent followed by recrystallisation from ethyl acetate affords the titled compound.
Workup
- temperatureto cool to room temperature
- customthe solvent removed in vacuo
- washThe residue is washed with saturated sodium bicarbonate solution (2×50 ml) and water (1×50 ml)
- extractionThe product is extracted with ethyl acetate (2×50 ml)
- dry with materialthe combined organic extracts dried (MgSO4)
- customRemoval of the solvent
- customfollowed by recrystallisation from ethyl acetate
Sources & evidence
- ORD record
- ord-ae1dfa604db74780b088a52302463771
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08129541B2
Linked notes
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