(4-Bromo-2-methanesulfonylphenyl)[4-(3,5,6-trimethylpyridin-2-yl)piperazin-1-yl]methanone → (S)-[2-methanesulfonyl-4-(4-methyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl][4-(3,5,6-trimethylpyridin-2-yl)piperazin-1-yl]methanone

HRID 2411432Notes

Reaction equation

HRID 2411432 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[C:29]([CH3:30])=[CH:28][C:27]([CH3:31])=[C:26]([CH3:32])[N:25]=3)[CH2:20][CH2:19]2)=[O:17])=[C:12]([S:33]([CH3:36])(=[O:35])=[O:34])[CH:11]=1>>[CH3:36][S:33]([C:12]1[CH:11]=[C:10]([N:4]2[CH2:3][C@H:2]([CH3:1])[CH2:6][S:5]2(=[O:8])=[O:7])[CH:15]=[CH:14][C:13]=1[C:16]([N:18]1[CH2:23][CH2:22][N:21]([C:24]2[C:29]([CH3:30])=[CH:28][C:27]([CH3:31])=[C:26]([CH3:32])[N:25]=2)[CH2:20][CH2:19]1)=[O:17])(=[O:35])=[O:34]

Participants

3

Reactant 2

HCID 58484785(4-Bromo-2-methanesulfonylphenyl)[4-(3,5,6-trimethylpyridin-2-yl)piperazin-1-yl]methanoneHCID 86676774(S)-4-methylisothiazolidine 1,1-dioxide

Product 1

HCID 71252059(S)-[2-methanesulfonyl-4-(4-methyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl][4-(3,5,6-trimethylpyridin-2-yl)piperazin-1-yl]methanoneYield 53.5%

Procedure

Using (S)-4-methylisothiazolidine 1,1-dioxide (110 mg) described in Preparation Example 4 and (4-bromo-2-methanesulfonylphenyl) [4-(3,5,6-trimethylpyridin-2-yl)piperazin-1-yl]methanone (253 mg) described in Preparation Example 122 and by the reaction and treatment in the same manner as in Example 4, the title compound (151 mg) was obtained.

Workup

  1. customdescribed in Preparation Example 122 and by the reaction and treatment in the same manner as in Example 4

Sources & evidence

ORD record
ord-443af7844d0444c7bd5838867e8885f2
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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