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

HRID 2411416Notes

Reaction equation

HRID 2411416 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.[CH3:17][C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:19]=1[N:25]1[CH2:30][CH2:29][N:28]([C:31]([C:33]2[CH:38]=[CH:37][C:36](I)=[CH:35][CH:34]=2)=[O:32])[CH2:27][CH2:26]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:36]1[CH:35]=[CH:34][C:33]([C:31]([N:28]2[CH2:27][CH2:26][N:25]([C:19]3[CH:20]=[CH:21][C:22]([CH3:24])=[CH:23][C:18]=3[CH3:17])[CH2:30][CH2:29]2)=[O:32])=[CH:38][CH:37]=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 58484733[4-(2,4-Dimethylphenyl)piperazin-1-yl](4-iodophenyl)methanone

Product 1

HCID 71251886(S)-[4-(3-benzyloxymethyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl][4-(2,4-dimethylphenyl)piperazin-1-yl]methanoneYield 88.6%

Procedure

Using (S)-3-benzyloxymethylisothiazolidine 1,1-dioxide (536 mg) described in Preparation Example 1 and [4-(2,4-dimethylphenyl)piperazin-1-yl](4-iodophenyl)methanone (933 mg) described in Preparation Example 108 and by the reaction and treatment in the same manner as in Example 1, (S)-[4-(3-benzyloxymethyl-1,1-dioxo-1λ6-isothiazolidin-2-yl)phenyl][4-(2,4-dimethylphenyl)piperazin-1-yl]methanone (1.05 g) was obtained. Using the obtained (S)-[4-(3-benzyloxymethyl-1,1-dioxo-1λ6-isothiazolidin-2-yl)phenyl][4-(2,4-dimethylphenyl)piperazin-1-yl]methanone (1.05 g) and by the reaction and treatment in the same manner as in Example 29, the title compound (590 mg) was obtained.

Workup

  1. customdescribed in Preparation Example 108 and by the reaction and treatment in the same manner as in Example 1

Sources & evidence

ORD record
ord-fedf2dc283b04f4b811a0d2a75b34ea9
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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