Hydrogen chloride-ethyl acetate → (S)-[4-(3-benzyloxymethyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl][4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone hydrochloride

HRID 2411413Notes

Reaction equation

HRID 2411413 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]1[CH2:14][CH2:13][S:12](=[O:16])(=[O:15])[N:11]1[C:17]1[CH:22]=[CH:21][C:20]([C:23]([N:25]2[CH2:30][CH2:29][N:28]([C:31]3[C:36]([CH3:37])=[CH:35][C:34]([CH3:38])=[CH:33][N:32]=3)[CH2:27][CH2:26]2)=[O:24])=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:39].C(OCC)(=O)C>C(OCC)(=O)C>[ClH:39].[CH2:1]([O:8][CH2:9][C@@H:10]1[CH2:14][CH2:13][S:12](=[O:15])(=[O:16])[N:11]1[C:17]1[CH:22]=[CH:21][C:20]([C:23]([N:25]2[CH2:26][CH2:27][N:28]([C:31]3[C:36]([CH3:37])=[CH:35][C:34]([CH3:38])=[CH:33][N:32]=3)[CH2:29][CH2:30]2)=[O:24])=[CH:19][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 71252269(S)-[4-(3-benzyloxymethyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl][4-(3,5-dimethyl-pyridin-2-yl)piperazin-1-yl]methanone

Product 1

HCID 71252268(S)-[4-(3-benzyloxymethyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl][4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-29ce660ec4b14026b7acc676ade55697
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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