[2'-(N-t-Butylsulfamoyl)biphenyl-4-yl]methyl bromide → 5-n-Butyl-4-[[2'-(N-t-butylsulfamoyl)biphenyl-4-yl]methyl]-2-[5-(carbomethoxy)-2-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 36256Notes

Reaction equation

HRID 36256 reaction equation
[CH2:1]([C:5]1[NH:6][C:7](=[O:21])[N:8]([C:10]2[CH:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[CH:12][C:11]=2[Cl:20])[N:9]=1)[CH2:2][CH2:3][CH3:4].[C:22]([NH:26][S:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[C:36]1[CH:41]=[CH:40][C:39]([CH2:42]Br)=[CH:38][CH:37]=1)(=[O:29])=[O:28])([CH3:25])([CH3:24])[CH3:23]>>[CH2:1]([C:5]1[N:6]([CH2:42][C:39]2[CH:40]=[CH:41][C:36]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=3[S:27](=[O:29])(=[O:28])[NH:26][C:22]([CH3:23])([CH3:25])[CH3:24])=[CH:37][CH:38]=2)[C:7](=[O:21])[N:8]([C:10]2[CH:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[CH:12][C:11]=2[Cl:20])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 15282100[2'-(N-t-Butylsulfamoyl)biphenyl-4-yl]methyl bromideHCID 1357200825-n-Butyl-2-[2-chloro-5-(methoxycarbonyl)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 104387175-n-Butyl-4-[[2'-(N-t-butylsulfamoyl)biphenyl-4-yl]methyl]-2-[5-(carbomethoxy)-2-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-oneYield 85%

Procedure

By the procedure of Example 13, Step A, 5-n-butyl-2-[5-(carbomethoxy)-2-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (from Step A) was alkylated with [2'-(N-t-butylsulfamoyl)biphenyl- 4-yl]methyl bromide (from Example 12, Step D). Flash chromatography of the crude product on silica gel (gradient elution with 0.5-5.0% MeOH in CH2Cl2) gave an 85% yield of the title compound as a white solid, mp 65°-67° C., homogeneous by TLC (98:2 CH2Cl2 --MeOH), mass spectrum (FAB) m/e 555 [M-(t-Bu)]+.

Sources & evidence

ORD record
ord-6bb8f9497ca9488eaca15fe3abfbbc83
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Reaction notes

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