Bromine → [5-(4-Chloro-3-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-(6-methoxy-pyridin-3-yl)-amine
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=O)[CH3:10])=[CH:4][C:3]=1[S:12]([CH3:15])(=[O:14])=[O:13].BrBr.BrC(C1C=CC(S(C)(=O)=O)=C(F)C=1)C(=O)C.[CH3:34][O:35][C:36]1[N:41]=[CH:40][C:39]([NH:42][C:43]([NH2:45])=[S:44])=[CH:38][CH:37]=1>O1CCOCC1.C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:44][C:43]([NH:42][C:39]3[CH:40]=[N:41][C:36]([O:35][CH3:34])=[CH:37][CH:38]=3)=[N:45][C:9]=2[CH3:10])=[CH:4][C:3]=1[S:12]([CH3:15])(=[O:14])=[O:13]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 10 °C
Procedure
1-(4-chloro-3-methanesulfonyl-phenyl)-propan-2-one (32b) (0.23 g, 1 mmol) is dissolved in dioxan (10 ml) and the solution is cooled to 10° C. at which point the mixture is semi-frozen. Bromine (0.045 ml, 0.8 mmol, 0.8 eq.) is added slowly and the mixture is stirred for an additional 15 minutes in a semi frozen state. The mixture is then allowed to warm to room temperature and the solvent is removed to give a brown oil containing starting material and 1-bromo-1-(3-fluoro-4-methanesulfonyl-phenyl)-propan-2-one. This material is dissolved in ethanol (10 ml). (6-Methoxy-pyridine-3-yl)-thiourea (0.183 g, 1 mmol) is added in one portion. The mixture is stirred at 60° C. for 30 minutes then allowed to cool whereupon the product crystallised. Filtration affords the titled compound as a white solid.
Workup
- temperaturefrozen state
- temperatureto warm to room temperature
- customthe solvent is removed
- customto give a brown oil
- additioncontaining
- stirringThe mixture is stirred at 60° C. for 30 minutes
- temperatureto cool whereupon the product
- customcrystallised
- filtrationFiltration
Sources & evidence
- ORD record
- ord-8c16f77ca23747c0addc418753520f43
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08017608B2
Reaction notes
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