HCID 15282102, compound → 5-n-Butyl-2,4-dihydro-2-isopropyl-4-[(2'-sulfamoylbiphenyl-4-yl)methyl]-3H-1,2,4-triazol-3-one

HRID 36190Notes

Reaction equation

HRID 36190 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[S:27](=[O:34])(=[O:33])[NH:28]C(C)(C)C)=[CH:17][CH:16]=2)[C:7](=[O:13])[N:8]([CH:10]([CH3:12])[CH3:11])[N:9]=1)[CH2:2][CH2:3][CH3:4]>C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>[CH2:1]([C:5]1[N:6]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[S:27](=[O:33])(=[O:34])[NH2:28])=[CH:17][CH:16]=2)[C:7](=[O:13])[N:8]([CH:10]([CH3:11])[CH3:12])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 15282102HCID 15282102, compound

Product 1

HCID 152821035-n-Butyl-2,4-dihydro-2-isopropyl-4-[(2'-sulfamoylbiphenyl-4-yl)methyl]-3H-1,2,4-triazol-3-oneYield 78.2%

Reagents, catalysts & solvents 2

HCID 7519AnisoleCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

Anisole (2 drops) was added to a solution of 5-n-butyl-4-[[2'-(N-t-butylsulfamoyl)biphenyl-4-yl]methyl]-2,4-dihydro-2-isopropyl-3H-1,2,4-triazol-3-one (from Step H) (97.5 mg; 0.201 mmole) in 2 ml of trifluoroacetic acid stirred under N2 at room temperature. After 24 hours, the solution was concentrated in vacuo. Chromatography of the residue on silica gel (gradient elution with 1.5 to 2% MeOH in CH2Cl2, containing 0.2% concentrated ammonium hydroxide) afforded 67.4 mg (78%) of the title compound as a white solid; satisfactory purity by TLC in 98:2:0.2 CH2Cl2 --MeOH-concd. NH4OH; mass spectrum (FAB) m/e 429 (M+1)+.

Workup

  1. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-559fa5ab7af244029676be34b451c1a0
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Reaction notes

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