Diisopropylethylamine → 3-[4-(4-Cyano-3-fluoro-phenyl)-piperazine-1-carbonyl]-4-hydroxy-benzenesulfonamide

HRID 2251280Notes

Reaction equation

HRID 2251280 reaction equation
COC1C=CC(C[O:8][C:9]2[CH:17]=[CH:16][C:15]([S:18](=[O:21])(=[O:20])[NH2:19])=[CH:14][C:10]=2[C:11]([OH:13])=O)=CC=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)[F:42].C(N(C(C)C)C(C)C)C.F[C:56]1[CH:57]=[C:58]([CH:61]=[CH:62][C:63]=1[N:64]1[CH2:69][CH2:68][NH:67][CH2:66][CH2:65]1)[C:59]#[N:60]>CN(C)C=O.C1COCC1>[C:59]([C:58]1[CH:61]=[CH:62][C:63]([N:64]2[CH2:69][CH2:68][N:67]([C:11]([C:10]3[CH:14]=[C:15]([S:18]([NH2:19])(=[O:20])=[O:21])[CH:16]=[CH:17][C:9]=3[OH:8])=[O:13])[CH2:66][CH2:65]2)=[CH:56][C:57]=1[F:42])#[N:60]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5961133-Fluoro-4-piperazin-1-yl-benzonitrileHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 690382462-(4-Methoxy-benzyloxy)-5-sulfamoyl-benzoic acid

Product 1

HCID 690384423-[4-(4-Cyano-3-fluoro-phenyl)-piperazine-1-carbonyl]-4-hydroxy-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.5 mmol 2-(4-methoxy-benzyloxy)-5-sulfamoyl-benzoic acid in 4 ml dimethylformamide and 12 ml THF were added 5.3 mmol TBTU, 17.5 mmol N-ethyldiisopropylamine and 3.5 mmol 3-fluoro-4-piperazin-1-yl-benzonitrile (WO9625414). The reaction was then stirred at RT for 1 h, concentrated in vacuo, and purified by chromatography on silica gel (eluant: ethyl acetate/heptane gradient) to afford the title compound. MS (m/e): 525.1 (M+H+)

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified by chromatography on silica gel (eluant: ethyl acetate/heptane gradient)

Sources & evidence

ORD record
ord-9695d6cb8eea4caaa75f7619015c8f72
Source dataset
uspto-grants-2008_01
Patent number
US07319099B2

Reaction notes

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