1-Allylpiperazine → N-[6-(4-Allylpiperazin-1-yl)pyrimidin-4-yl]-4-isopropylbenzenesulfonamide

HRID 444972Notes

Reaction equation

HRID 444972 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

HCID 8064221-AllylpiperazineHCID 86003781HCID 86003781, compound

Product 1

HCID 69145389N-[6-(4-Allylpiperazin-1-yl)pyrimidin-4-yl]-4-isopropylbenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

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

  1. stirringSubsequently, the reaction mixture was stirred at 100° C., in a microwave oven, for 45 minutes
  2. extractionAfter that, the aqueous reaction mixture was extracted with 50 ml of ethyl acetate
  3. filtrationthe precipitate was filtered off with suction, with 190 mg (34% of theory) of the title compound
  4. custombeing obtained

Sources & evidence

ORD record
ord-5c3dbaeeb53b4a388bda7136820bad7f
Source dataset
uspto-grants-2013_07
Patent number
US08476275B2

Reaction notes

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