(4-Bromo-2-methanesulfonylphenyl)[4-(2,4-dimethylphenyl)piperazin-1-yl]methanone → (S)-[4-(2,4-dimethylphenyl)piperazin-1-yl][4-(3-isopropyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)-2-methanesulfonylphenyl]methanone

HRID 2411398Notes

Reaction equation

HRID 2411398 reaction equation
[CH:1]([C@@H:4]1[CH2:8][CH2:7][S:6](=[O:10])(=[O:9])[NH:5]1)([CH3:3])[CH3:2].Br[C:12]1[CH:17]=[CH:16][C:15]([C:18]([N:20]2[CH2:25][CH2:24][N:23]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][C:27]=3[CH3:33])[CH2:22][CH2:21]2)=[O:19])=[C:14]([S:34]([CH3:37])(=[O:36])=[O:35])[CH:13]=1>>[CH3:33][C:27]1[CH:28]=[C:29]([CH3:32])[CH:30]=[CH:31][C:26]=1[N:23]1[CH2:22][CH2:21][N:20]([C:18]([C:15]2[CH:16]=[CH:17][C:12]([N:5]3[C@H:4]([CH:1]([CH3:3])[CH3:2])[CH2:8][CH2:7][S:6]3(=[O:10])=[O:9])=[CH:13][C:14]=2[S:34]([CH3:37])(=[O:36])=[O:35])=[O:19])[CH2:25][CH2:24]1

Participants

3

Reactant 2

HCID 58484856(4-Bromo-2-methanesulfonylphenyl)[4-(2,4-dimethylphenyl)piperazin-1-yl]methanoneHCID 86676751(S)-3-isopropylisothiazolidine 1,1-dioxide

Product 1

HCID 71252323(S)-[4-(2,4-dimethylphenyl)piperazin-1-yl][4-(3-isopropyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)-2-methanesulfonylphenyl]methanoneYield 24.4%

Procedure

Using (S)-3-isopropylisothiazolidine 1,1-dioxide (320 mg) described in Preparation Example 6 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 4, the title compound (130 mg) was obtained.

Workup

  1. customdescribed in Preparation Example 110 and by the reaction and treatment in the same manner as in Example 4

Sources & evidence

ORD record
ord-144609350b4f4b5c91c170347e17d398
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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