Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → N-(5-chloro-3-methoxypyrazin-2-yl)-4'-hydroxy-N-(isobutoxycarbonyl)-2-biphenylsulphonamide

HRID 1378356Notes

Reaction equation

HRID 1378356 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([O:38][CH3:39])[C:5]([N:8]([C:31]([O:33][CH2:34][CH:35]([CH3:37])[CH3:36])=[O:32])[S:9]([C:12]2[C:13]([C:18]3[CH:23]=[CH:22][C:21]([O:24]C4CCCCO4)=[CH:20][CH:19]=3)=[CH:14][CH:15]=[CH:16][CH:17]=2)(=[O:11])=[O:10])=[N:6][CH:7]=1.[NH+]1C=CC=CC=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1>C(O)C>[Cl:1][C:2]1[N:3]=[C:4]([O:38][CH3:39])[C:5]([N:8]([C:31]([O:33][CH2:34][CH:35]([CH3:37])[CH3:36])=[O:32])[S:9]([C:12]2[C:13]([C:18]3[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=3)=[CH:14][CH:15]=[CH:16][CH:17]=2)(=[O:11])=[O:10])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 53756881HCID 53756881, compound

Product 1

HCID 22911291N-(5-chloro-3-methoxypyrazin-2-yl)-4'-hydroxy-N-(isobutoxycarbonyl)-2-biphenylsulphonamideYield 97.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(5-Chloro-3-methoxypyrazin-2-yl)- N-(isobutoxycarbonyl)-4'-[2-(2 H)-tetrahydropyranyloxy]-2-biphenylsulphonamide (1.15 g) and pyridinium-p-toluenesulphonate (50 mg) in ethanol (50 ml) was heated at 60° C. for 3 hours. Volatile material was removed by evaporation and the residue was triturated with etherexane (1:1 v/v) to give N-(5-chloro-3-methoxypyrazin-2-yl)-4'-hydroxy- N-(isobutoxycarbonyl)-2-biphenylsulphonamide (0.96 g), m.p. 175°-177° C.; microanalysis found: C, 53.9; H, 4.8; N, 8.2%; C21H22C1N3O6 requires: C, 53.7; H, 4.5; N, 8.5%.

Workup

  1. customVolatile material was removed by evaporation
  2. customthe residue was triturated with etherexane (1:1 v/v)

Sources & evidence

ORD record
ord-2a231f1f8cee4e5bb2d0d4d0d041e51e
Source dataset
uspto-grants-1997_09
Patent number
US05668137

Reaction notes

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