1-(3,5-Dimethylpyridin-2-yl)piperazine → (R)-[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl][4-(3-methyl-1,1-dioxo-1lambda6-isothiazolidin-2-ylmethyl)phenyl]methanone

HRID 2411623Notes

Reaction equation

HRID 2411623 reaction equation
[CH3:1][C@@H:2]1[CH2:6][CH2:5][S:4](=[O:8])(=[O:7])[N:3]1[CH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=O)=[CH:12][CH:11]=1.[CH3:20][C:21]1[C:22]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[N:23][CH:24]=[C:25]([CH3:27])[CH:26]=1>>[CH3:20][C:21]1[C:22]([N:28]2[CH2:29][CH2:30][N:31]([C:14]([C:13]3[CH:12]=[CH:11][C:10]([CH2:9][N:3]4[C@H:2]([CH3:1])[CH2:6][CH2:5][S:4]4(=[O:7])=[O:8])=[CH:19][CH:18]=3)=[O:16])[CH2:32][CH2:33]2)=[N:23][CH:24]=[C:25]([CH3:27])[CH:26]=1

Participants

3

Reactant 2

HCID 584844961-(3,5-Dimethylpyridin-2-yl)piperazineHCID 71261169methyl (R)-4-(3-methyl-1,1-dioxo-1lambda6-isothiazolidin-2-ylmethyl)benzoate

Product 1

HCID 71252277(R)-[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl][4-(3-methyl-1,1-dioxo-1lambda6-isothiazolidin-2-ylmethyl)phenyl]methanoneYield 78.3%

Procedure

Using methyl (R)-4-(3-methyl-1,1-dioxo-1λ6-isothiazolidin-2-ylmethyl)benzoate (79 mg) described in Preparation Example 42 and 1-(3,5-dimethylpyridin-2-yl)piperazine (53 mg) described in Preparation Example 79 and by the reaction and treatment in the same manner as in Example 109, the title compound (96 mg) was obtained.

Workup

  1. customdescribed in Preparation Example 79 and by the reaction and treatment in the same manner as in Example 109

Sources & evidence

ORD record
ord-b129462cb75344c8b1108c316275ca77
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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