(4-Bromo-2-methanesulfonylphenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone → (S)-[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl][4-(3-isopropyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)-2-methanesulfonylphenyl]methanone

HRID 2411408Notes

Reaction equation

HRID 2411408 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[C:31]([CH3:32])=[CH:30][C:29]([CH3:33])=[CH:28][N:27]=3)[CH2:22][CH2:21]2)=[O:19])=[C:14]([S:34]([CH3:37])(=[O:36])=[O:35])[CH:13]=1>>[CH3:32][C:31]1[C:26]([N:23]2[CH2:24][CH2:25][N:20]([C:18]([C:15]3[CH:16]=[CH:17][C:12]([N:5]4[C@H:4]([CH:1]([CH3:3])[CH3:2])[CH2:8][CH2:7][S:6]4(=[O:10])=[O:9])=[CH:13][C:14]=3[S:34]([CH3:37])(=[O:36])=[O:35])=[O:19])[CH2:21][CH2:22]2)=[N:27][CH:28]=[C:29]([CH3:33])[CH:30]=1

Participants

3

Reactant 2

HCID 58484505(4-Bromo-2-methanesulfonylphenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanoneHCID 86676751(S)-3-isopropylisothiazolidine 1,1-dioxide

Product 1

HCID 71253077(S)-[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl][4-(3-isopropyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)-2-methanesulfonylphenyl]methanoneYield 26.6%

Procedure

Using (S)-3-isopropylisothiazolidine 1,1-dioxide (240 mg) described in Preparation Example 6 and (4-bromo-2-methanesulfonylphenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone (452 mg) described in Preparation Example 112 and by the reaction and treatment in the same manner as in Example 4, the title compound (142 mg) was obtained.

Workup

  1. customdescribed in Preparation Example 112 and by the reaction and treatment in the same manner as in Example 4

Sources & evidence

ORD record
ord-7fb4fb7e2bac490a81d2bc0f8d237120
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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