(S)-3-benzyloxymethylisothiazolidine 1,1-dioxide → (S)-[4-(3-benzyloxymethyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl][4-(3,5-dimethyl-pyridin-2-yl)piperazin-1-yl]methanone

HRID 2411412Notes

Reaction equation

HRID 2411412 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[C:19]([N:25]2[CH2:30][CH2:29][N:28]([C:31]([C:33]3[CH:38]=[CH:37][C:36](I)=[CH:35][CH:34]=3)=[O:32])[CH2:27][CH2:26]2)=[N:20][CH:21]=[C:22]([CH3:24])[CH:23]=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:37]=[CH:38][C:33]([C:31]([N:28]2[CH2:29][CH2:30][N:25]([C:19]3[C:18]([CH3:17])=[CH:23][C:22]([CH3:24])=[CH:21][N:20]=3)[CH2:26][CH2:27]2)=[O:32])=[CH:34][CH:35]=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 58484535[4-(3,5-Dimethylpyridin-2-yl)piperazin-1-yl](4-iodophenyl)methanone

Product 1

HCID 71252269(S)-[4-(3-benzyloxymethyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl][4-(3,5-dimethyl-pyridin-2-yl)piperazin-1-yl]methanoneYield 77.2%

Procedure

Using (S)-3-benzyloxymethylisothiazolidine 1,1-dioxide (287 mg) described in Preparation Example 1 and [4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl](4-iodophenyl)methanone (500 mg) described in Preparation Example 113 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-(3,5-dimethyl-pyridin-2-yl)piperazin-1-yl]methanone (490 mg) was obtained. The obtained (S)-[4-(3-benzyloxymethyl-1,1-dioxo-1λ6-isothiazolidin-2-yl)phenyl][4-(3,5-dimethyl-pyridin-2-yl)piperazin-1-yl]methanone (490 mg) was dissolved in ethyl acetate, 4N hydrogen chloride/ethyl acetate was added, and the precipitate was collected by filtration to give the title compound (410 mg).

Workup

  1. customdescribed in Preparation Example 113 and by the reaction and treatment in the same manner as in Example 1

Sources & evidence

ORD record
ord-8d4a290c0f1644fdb3e640956f4b0cbb
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

Loading…