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

HRID 2411561Notes

Reaction equation

HRID 2411561 reaction equation
[O:1]=[S:2]1(=[O:38])[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:12]=[C:11]([N:13]2[CH2:17][CH2:16][CH2:15][S:14]2(=[O:19])=[O:18])[CH:10]=[CH:9][C:8]=1[C:20]([N:22]1[CH2:27][CH2:26][N:25]([C:28]2[C:33]([CH:34]3[CH2:36][CH2:35]3)=[CH:32][C:31]([CH3:37])=[CH:30][N:29]=2)[CH2:24][CH2:23]1)=[O:21].[ClH:39].C(OCC)(=O)C>C(OCC)(=O)C>[ClH:39].[O:38]=[S:2]1(=[O:1])[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:12]=[C:11]([N:13]2[CH2:17][CH2:16][CH2:15][S:14]2(=[O:19])=[O:18])[CH:10]=[CH:9][C:8]=1[C:20]([N:22]1[CH2:23][CH2:24][N:25]([C:28]2[C:33]([CH:34]3[CH2:36][CH2:35]3)=[CH:32][C:31]([CH3:37])=[CH:30][N:29]=2)[CH2:26][CH2:27]1)=[O:21]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 71252172[2,4-Bis(1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl][4-(3-cyclopropyl-5-methylpyridin-2-yl)piperazin-1-yl]methanone

Product 1

HCID 86676781[2,4-Bis(1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl][4-(3-cyclopropyl-5-methylpyridin-2-yl)piperazin-1-yl]methanone hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2,4-Bis(1,1-dioxo-1λ6-isothiazolidin-2-yl)benzoic acid (200 mg) described in Preparation Example 34, 1-(3-cyclopropyl-5-methylpyridin-2-yl)piperazine (121 mg) described in Preparation Example 86, and 1-hydroxybenzotriazole 1 hydrate (79 mg) were dissolved in N,N-dimethylformamide (3 mL), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (112 mg) was added, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (ethyl acetate:hexane) to give [2,4-bis(1,1-dioxo-1λ6-isothiazolidin-2-yl)phenyl][4-(3-cyclopropyl-5-methylpyridin-2-yl)piperazin-1-yl]methanone. The obtained [2,4-bis(1,1-dioxo-1λ6-isothiazolidin-2-yl)phenyl][4-(3-cyclopropyl-5-methylpyridin-2-yl)piperazin-1-yl]methanone (240 mg) was dissolved in ethyl acetate, 4N hydrogen chloride/ethyl acetate (0.11 mL) was added, and the precipitate was collected by filtration to give the title compound (104 mg).

Workup

  1. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-f410dd1a3dd0465bb460b646bd5cb5c7
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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