Diisopropylethylamine → 4-(4-((4'-Chlorobiphenyl-2-yl)methyl)piperazin-1-yl)-2-fluorobenzenesulfonamide

HRID 1848843Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[S:9]([NH2:12])(=[O:11])=[O:10].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH2:26][N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[CH:16][CH:15]=1.C(N(CC)C(C)C)(C)C>CS(C)=O.C(OCC)(=O)C>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH2:26][N:27]2[CH2:28][CH2:29][N:30]([C:6]3[CH:5]=[CH:4][C:3]([S:9]([NH2:12])(=[O:11])=[O:10])=[C:2]([F:1])[CH:7]=3)[CH2:31][CH2:32]2)=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 2,4-difluorobenzenesulfonamide (1.56 g) and 1-((4′-chlorobiphenyl-2-yl)methyl)piperazine (2.32 g) in dimethylsulfoxide (20 mL) was added N,N-diisopropylethylamine (5 mL). The mixture was stirred at 120° C. overnight. The mixture was diluted with ethyl acetate (300 mL) and washed with water (3×) brine and dried over Na2SO4. After filtration and evaporation of the solvent, the residue was loaded on a column and eluted with 40% ethyl acetate in hexane to give the title compound.

Workup

washwashed with water (3×) brine
dry with materialdried over Na2SO4
filtrationAfter filtration and evaporation of the solvent
washeluted with 40% ethyl acetate in hexane

Sources & evidence

ORD record: ord-e5d21e09030749808107654fc1c1f91a
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952157B2

Reaction notes

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