3-{3-Butyl-4-[2''-(2-chloro-benzoylsulfamoyl)-biphenyl-4-ylmethyl]-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}-4-chloro-benzoic acid methyl ester → 5-n-Butyl-2-[5-(N-n-butylcarbamoyl)-2-chlorophenyl]-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]biphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3one

HRID 36259Notes

Reaction equation

HRID 36259 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[S:35](=[O:47])(=[O:46])[NH:36][C:37](=[O:45])[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[Cl:44])=[CH:25][CH:24]=2)[C:7](=[O:21])[N:8]([C:10]2[CH:15]=[C:14]([C:16](OC)=[O:17])[CH:13]=[CH:12][C:11]=2[Cl:20])[N:9]=1)[CH2:2][CH2:3][CH3:4]>C(N)CCC>[CH2:1]([C:5]1[N:6]([CH2:22][C:23]2[CH:24]=[CH:25][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[S:35](=[O:46])(=[O:47])[NH:36][C:37](=[O:45])[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[Cl:44])=[CH:27][CH:28]=2)[C:7](=[O:21])[N:8]([C:10]2[CH:15]=[C:14]([C:16](=[O:17])[NH:6][CH2:5][CH2:1][CH2:2][CH3:3])[CH:13]=[CH:12][C:11]=2[Cl:20])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 1

HCID 103724973-{3-Butyl-4-[2''-(2-chloro-benzoylsulfamoyl)-biphenyl-4-ylmethyl]-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}-4-chloro-benzoic acid methyl ester

Product 1

HCID 104851165-n-Butyl-2-[5-(N-n-butylcarbamoyl)-2-chlorophenyl]-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]biphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3oneYield 186.7%

Reagents, catalysts & solvents 1

HCID 8007ButylamineSolvent

Procedure

A solution of 100 mg (0.14 mmole) of 5-n-butyl-2-[5-(carbomethoxy)-2-chlorophenyl]-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]biphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (from Step D), in 1 mL of n-butylamine was stirred at 65° C. overnight. After removal of excess n-butylamine, the crude product was flash chromatographed over silica gel (gradient elution with 0.5-5.0% MeOH/CH2Cl2) to give 96 mg (91%) of the desired product as a white solid, mp >155° C. (gradual), homogeneous by TLC in 95:5 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 734 (M+1)+.

Workup

  1. customAfter removal of excess n-butylamine
  2. customchromatographed over silica gel (gradient elution with 0.5-5.0% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-76f707944c81415c8af0d7783548c431
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Reaction notes

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