(S)-3-benzyloxymethylisothiazolidine 1,1-dioxide → (S)-[6-(3-benzyloxymethyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)pyridin-3-yl][4-(2,4-dimethylphenyl)piperazin-1-yl]methanone

HRID 2411415Notes

Reaction equation

HRID 2411415 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]1[CH2:14][CH2:13][S:12](=[O:16])(=[O:15])[NH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:18]1[N:23]=[CH:22][C:21]([C:24]([N:26]2[CH2:31][CH2:30][N:29]([C:32]3[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][C:33]=3[CH3:39])[CH2:28][CH2:27]2)=[O:25])=[CH:20][CH:19]=1>>[CH2:1]([O:8][CH2:9][C@@H:10]1[CH2:14][CH2:13][S:12](=[O:16])(=[O:15])[N:11]1[C:18]1[N:23]=[CH:22][C:21]([C:24]([N:26]2[CH2:27][CH2:28][N:29]([C:32]3[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][C:33]=3[CH3:39])[CH2:30][CH2:31]2)=[O:25])=[CH:20][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 16664117(S)-3-benzyloxymethylisothiazolidine 1,1-dioxideHCID 58484755HCID 58484755, compound

Product 1

HCID 71252888(S)-[6-(3-benzyloxymethyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)pyridin-3-yl][4-(2,4-dimethylphenyl)piperazin-1-yl]methanoneYield 61.4%

Procedure

Using (S)-3-benzyloxymethylisothiazolidine 1,1-dioxide (536 mg) described in Preparation Example 1 and (6-bromopyridin-3-yl) [4-(2,4-dimethylphenyl)piperazin-1-yl]methanone (831 mg) described in Preparation Example 115 and by the reaction and treatment in the same manner as in Example 4, the title compound (729 mg) was obtained.

Workup

  1. customdescribed in Preparation Example 115 and by the reaction and treatment in the same manner as in Example 4

Sources & evidence

ORD record
ord-96806db58c724d0c83bf4f051f27bd4e
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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