(4-Bromo-2-methanesulfonylphenyl)[4-(2,4-dimethylphenyl)piperazin-1-yl]methanone → (S)-[4-(2,4-dimethylphenyl)piperazin-1-yl][2-methanesulfonyl-4-(4-methyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl]methanone

HRID 2411394Notes

Reaction equation

HRID 2411394 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=3[CH3:23])[CH2:12][CH2:11]2)=[O:9])=[C:4]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:3]=1.[CH3:28][C@@H:29]1[CH2:33][S:32](=[O:35])(=[O:34])[NH:31][CH2:30]1>>[CH3:23][C:17]1[CH:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:16]=1[N:13]1[CH2:14][CH2:15][N:10]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([N:31]3[CH2:30][C@H:29]([CH3:28])[CH2:33][S:32]3(=[O:35])=[O:34])=[CH:3][C:4]=2[S:24]([CH3:27])(=[O:26])=[O:25])=[O:9])[CH2:11][CH2:12]1

Participants

3

Reactant 2

HCID 58484856(4-Bromo-2-methanesulfonylphenyl)[4-(2,4-dimethylphenyl)piperazin-1-yl]methanoneHCID 86676774(S)-4-methylisothiazolidine 1,1-dioxide

Product 1

HCID 71252933(S)-[4-(2,4-dimethylphenyl)piperazin-1-yl][2-methanesulfonyl-4-(4-methyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl]methanoneYield 27.2%

Procedure

Using (4-bromo-2-methanesulfonylphenyl)[4-(2,4-dimethylphenyl)piperazin-1-yl]methanone (534 mg) described in Preparation Example 110 and (S)-4-methylisothiazolidine 1,1-dioxide (320 mg) described in Preparation Example 4 and by the reaction and treatment in the same manner as in Example 4, the title compound (163 mg) was obtained.

Workup

  1. customdescribed in Preparation Example 4 and by the reaction and treatment in the same manner as in Example 4

Sources & evidence

ORD record
ord-e996c24d6d3b4edc82b376f5e83a04fd
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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