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

HRID 2411402Notes

Reaction equation

HRID 2411402 reaction equation
[CH3:1][C@H:2]1[CH2:6][S:5](=[O:8])(=[O:7])[NH:4][CH2:3]1.Br[C:10]1[CH:15]=[CH:14][C:13]([C:16]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:25]=3[CH3:31])[CH2:20][CH2:19]2)=[O:17])=[C:12]([S:32]([CH3:35])(=[O:34])=[O:33])[CH:11]=1>>[CH3:31][C:25]1[CH:26]=[C:27]([CH3:30])[CH:28]=[CH:29][C:24]=1[N:21]1[CH2:20][CH2:19][N:18]([C:16]([C:13]2[CH:14]=[CH:15][C:10]([N:4]3[CH2:3][C@@H:2]([CH3:1])[CH2:6][S:5]3(=[O:8])=[O:7])=[CH:11][C:12]=2[S:32]([CH3:35])(=[O:34])=[O:33])=[O:17])[CH2:23][CH2:22]1

Participants

3

Reactant 2

HCID 58484856(4-Bromo-2-methanesulfonylphenyl)[4-(2,4-dimethylphenyl)piperazin-1-yl]methanoneHCID 86676775(R)-4-methylisothiazolidine 1,1-dioxide

Product 1

HCID 71252453(R)-[4-(2,4-dimethylphenyl)piperazin-1-yl][2-methanesulfonyl-4-(4-methyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl]methanoneYield 4.6%

Procedure

Using (R)-4-methylisothiazolidine 1,1-dioxide (203 mg) described in Preparation Example 7 and (4-bromo-2-methanesulfonylphenyl)[4-(2,4-dimethylphenyl)piperazin-1-yl]methanone (451 mg) described in Preparation Example 110 and by the reaction and treatment in the same manner as in Example 1, the title compound (23 mg) was obtained.

Workup

  1. customdescribed in Preparation Example 110 and by the reaction and treatment in the same manner as in Example 1

Sources & evidence

ORD record
ord-f7469ec7fe4f44128550e5349ba041ba
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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