1-Allylpiperazine → N-[6-(4-Allylpiperazin-1-yl)pyrimidin-4-yl]-4-isopropylbenzenesulfonamide
Reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:3]=1.[CH2:21]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)[CH:22]=[CH2:23]>CS(C)=O.O>[CH2:21]([N:24]1[CH2:29][CH2:28][N:27]([C:2]2[N:7]=[CH:6][N:5]=[C:4]([NH:8][S:9]([C:12]3[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=3)(=[O:11])=[O:10])[CH:3]=2)[CH2:26][CH2:25]1)[CH:22]=[CH2:23]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
430 mg (1.38 mmol) of N-(6-chloropyrimidin-4-yl)-4-isopropylbenzenesulfonamide from Example 18.1 were dissolved in 3 ml of dimethyl sulfoxide, after which 1.74 g (13.79 mmol) of N-allylpiperazine were added and the mixture was stirred overnight. Subsequently, the reaction mixture was stirred at 100° C., in a microwave oven, for 45 minutes. After the reaction mixture had cooled down to room temperature, it was diluted with 50 ml of water. After that, the aqueous reaction mixture was extracted with 50 ml of ethyl acetate and the precipitate was filtered off with suction, with 190 mg (34% of theory) of the title compound being obtained.
Workup
- stirringSubsequently, the reaction mixture was stirred at 100° C., in a microwave oven, for 45 minutes
- extractionAfter that, the aqueous reaction mixture was extracted with 50 ml of ethyl acetate
- filtrationthe precipitate was filtered off with suction, with 190 mg (34% of theory) of the title compound
- custombeing obtained
Sources & evidence
- ORD record
- ord-8ef161cc90244caf87c572103c96bed7
- Source dataset
- uspto-grants-2008_01
- Patent number
- US07320979B2
Reaction notes
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