HCID 18704817, compound → HCID 18704789, compound

HRID 343398Notes

Reaction equation

HRID 343398 reaction equation
C([C:5]1[CH:6]=[C:7]([S:20]([NH:23][C:24]2[C:29]([O:30][CH3:31])=[N:28][C:27]([CH3:32])=[CH:26][N:25]=2)(=[O:22])=[O:21])[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-])=O)[CH:12]=2)=[CH:9][CH:10]=1)C(C)C>CO.O.[Pd]>[NH2:17][C:13]1[CH:12]=[C:11]([C:8]2[C:7]([S:20]([NH:23][C:24]3[C:29]([O:30][CH3:31])=[N:28][C:27]([CH3:32])=[CH:26][N:25]=3)(=[O:21])=[O:22])=[CH:6][CH:5]=[CH:10][CH:9]=2)[CH:16]=[CH:15][C:14]=1[CH2:7][CH:8]([CH3:11])[CH3:9]

Participants

4

Reactant 1

HCID 18704817HCID 18704817, compound

Product 1

HCID 18704789HCID 18704789, compoundYield 65.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

4-Isobutyl-N-(3-methoxy-5-methyl-2-pyrazinyl)-3'-nitro-2-biphenylsulphonamide (0.456 g) was dissolved in methanol/water (1:9 v/v; 10 ml) and the solution was catalytically hydrogenated over 10% Pd-C (0.046 g). The catalyst was removed by filtration through diatomaceous earth and the residue was purified by elution with ethyl acetate/hexane (1:3 v/v) through a silica gel Mega Bond Elut column. The resulting foam was recrystallised from ether to give 3'-amino-4'-isobutyl-N-(3-methoxy-5-methyl-2-pyrazinyl)-2-biphenylsulphonamide (0.14 g), m.p. 160°-162° C.; mass spectrum (+ve FAB, DMSO/methanol/NBA): 427 (M+H)+.

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. customthe residue was purified by elution with ethyl acetate/hexane (1:3 v/v) through a silica gel Mega Bond Elut column
  3. customThe resulting foam was recrystallised from ether

Sources & evidence

ORD record
ord-03100ab844c34265af5c14523052d0e6
Source dataset
uspto-grants-1999_01
Patent number
US05861401

Reaction notes

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