4''-[3-Butyl-1-(2-chloro-phenyl)-5-oxo-1,5-dihydro-[1,2,4]triazol-4-ylmethyl]-biphenyl-2-sulfonic acid tert-butylamide → 4''-[3-Butyl-1-(2-chloro-phenyl)-5-oxo-1,5-dihydro-[1,2,4]triazol-4-ylmethyl]-biphenyl-2-sulfonic acid amide

HRID 36193Notes

Reaction equation

HRID 36193 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[S:31](=[O:38])(=[O:37])[NH:32]C(C)(C)C)=[CH:21][CH:20]=2)[C:7](=[O:17])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])[N:9]=1)[CH2:2][CH2:3][CH3:4]>FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>[CH2:1]([C:5]1[N:6]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[S:31](=[O:37])(=[O:38])[NH2:32])=[CH:21][CH:20]=2)[C:7](=[O:17])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 117573574''-[3-Butyl-1-(2-chloro-phenyl)-5-oxo-1,5-dihydro-[1,2,4]triazol-4-ylmethyl]-biphenyl-2-sulfonic acid tert-butylamide

Product 1

HCID 100288154''-[3-Butyl-1-(2-chloro-phenyl)-5-oxo-1,5-dihydro-[1,2,4]triazol-4-ylmethyl]-biphenyl-2-sulfonic acid amideYield 89.2%

Reagents, catalysts & solvents 2

HCID 7519AnisoleCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 122 mg (0.221 mmole) of 5-n-butyl-4-[[2'-(N-t-butylsulfamoyl)biphenyl-4-yl]methyl]-2-(2-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one in 2.2 ml of anhydrous trifluoroacetic acid (TFA) containing 2 drops of anisole was stirred at room temperature under N2 for 2 days. The TFA was removed under a gentle stream of N2 followed by co-evaporation in vacuo 2× with toluene. The residue was chromatographed on a silica gel column (gradient elution with 0.5-2% MeOH in CH2Cl2). Concentration of the combined product fractions gave 98 mg (89%) of the title compound as a white solid, mp 140°-142° C.; satisfactory purity by TLC in 98:2 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 497 (M+1)+.

Workup

  1. customThe TFA was removed under a gentle stream of N2
  2. customThe residue was chromatographed on a silica gel column (gradient elution with 0.5-2% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-a52e2e305c0e46cb95234486fa249076
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Reaction notes

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