Ethanol → [5-(3-Fluoro-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-(1H-pyrazol-3-yl)-amine
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:12][C:13](=O)[CH3:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].BrBr.C(O)C.[NH:21]1[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH2:29])=[S:28])=[N:22]1>O1CCOCC1.C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C:12]2[S:28][C:27]([NH:26][C:23]3[CH:24]=[CH:25][NH:21][N:22]=3)=[N:29][C:13]=2[CH3:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 10 °C
Procedure
1-(3-Fluoro-4-methanesulfonyl-phenyl)-propan-2-one (68c) (6.0 g, 26 mmol) is dissolved in dioxan (50 ml) and the solution is cooled to 10° C. at which point the mixture is semi frozen. A solution of bromine (0.9 ml, 17 mmol) in chloroform (2 ml) is added slowly over 30 minutes 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 red oil. Ethanol (70 ml) and (1H-pyrazol-3-yl)-thiourea (35a) (3.2 g, 22 mmol) are added and the reaction is stirred at 60° C. for 30 minutes. The solution is allowed to cool to room temperature whereupon the product crystallises. Filtration affords the titled compound.
Workup
- temperatureis semi frozen
- temperaturefrozen state
- temperatureto warm to room temperature
- customthe solvent is removed
- customto give a red oil
- stirringthe reaction is stirred at 60° C. for 30 minutes
- temperatureto cool to room temperature whereupon the product
- customcrystallises
- filtrationFiltration
Sources & evidence
- ORD record
- ord-658e686f628d41828ce511394373a426
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08017608B2
Reaction notes
Loading…