(2-Bromo-4-chlorophenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone → (R)-[4-chloro-2-(3-methyl-1,1-dioxoisothiazolidin-2-yl)phenyl][4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone

HRID 1804072Notes

Reaction equation

HRID 1804072 reaction equation
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][N:18]=2)[CH2:13][CH2:12]1)=[O:10].[CH3:25][CH:26]1[CH2:30][CH2:29][S:28](=[O:32])(=[O:31])[NH:27]1>>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][N:18]=3)[CH2:13][CH2:12]2)=[O:10])=[C:2]([N:27]2[C@H:26]([CH3:25])[CH2:30][CH2:29][S:28]2(=[O:32])=[O:31])[CH:7]=1

Participants

3

Reactant 2

HCID 58484730(2-Bromo-4-chlorophenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanoneHCID 673808143-Methyl-1,2-thiazolidine 1,1-dioxide

Product 1

HCID 58484709(R)-[4-chloro-2-(3-methyl-1,1-dioxoisothiazolidin-2-yl)phenyl][4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanoneYield 20.6%

Procedure

By reaction and treatment in the same manner as in Preparation Example 12 and using (2-bromo-4-chlorophenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone (408.7 mg) described in Preparation Example 119 and 3-methylisothiazolidine-1,1-dioxide (135 mg), the title compound (95.1 mg) was obtained.

Workup

  1. customBy reaction and treatment in the same manner
  2. customas in Preparation Example 12

Sources & evidence

ORD record
ord-779326eb3b2e45c8a7443e210d2678cb
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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