Hydrochloric Acid → [4-Bromo-2-(1,1-dioxoisothiazolidin-2-yl)phenyl][4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone

HRID 1804065Notes

Reaction equation

[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=O)=[C:4]([N:12]2[CH2:16][CH2:15][CH2:14][S:13]2(=[O:18])=[O:17])[CH:3]=1.[OH-].[Na+].Cl.[CH3:22][C:23]1[C:24]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[N:25][CH:26]=[C:27]([CH3:29])[CH:28]=1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1>CO.O>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([N:33]2[CH2:34][CH2:35][N:30]([C:24]3[C:23]([CH3:22])=[CH:28][C:27]([CH3:29])=[CH:26][N:25]=3)[CH2:31][CH2:32]2)=[O:8])=[C:4]([N:12]2[CH2:16][CH2:15][CH2:14][S:13]2(=[O:18])=[O:17])[CH:3]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To methyl 4-bromo-2-(1,1-dioxoisothiazolidin-2-yl)benzoate (2 g) described in Preparation Example 116 were added 1N aqueous sodium hydroxide solution (9 mL) and methanol (18 mL), and the mixture was stirred at 60-70° C. 1N hydrochloric acid (9 mL) was added, a solution of 1-(3,5-dimethylpyridin-2-yl)piperazine (1.14 g) described in Preparation Example 47 in methanol (2 mL) and 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (DMT-MM) (1.65 g) were 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. After evaporation of the solvent, the residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (2.4 g).

Workup

stirringthe mixture was stirred at room temperature overnight
extractionthe mixture was extracted with ethyl acetate
customAfter evaporation of the solvent
customthe residue was purified by column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record: ord-0942c41825b241d28e1d6abbd6c64dda
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354401B2

Reaction notes

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