2-Chlorobenzoic Acid → 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

HRID 36258

Reaction equation

HRID 36258 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:38])(=[O:37])[NH2:36])=[CH:25][CH:24]=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].[Cl:39][C:40]1[CH:48]=[CH:47][CH:46]=[CH:45][C:41]=1[C:42](O)=[O:43].C1N=CN(C(N2C=NC=C2)=O)C=1.C1CCN2C(=NCCC2)CC1>>[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:38])(=[O:37])[NH:36][C:42](=[O:43])[C:41]3[CH:45]=[CH:46][CH:47]=[CH:48][C:40]=3[Cl:39])=[CH:25][CH:24]=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

5

Reactant 4

HCID 83742-Chlorobenzoic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 99851435-n-Butyl-2-[5-(carbomethoxy)-2-chlorophenyl]-2,4-dihydro-4-[(2'-sulfamoylbiphenyl-4-yl)methyl]-3H-1,2,4,-triazol-3-one

Product 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

Procedure

The title compound was prepared from 5-n-butyl-2-[5-(carbomethoxy)-2-chlorophenyl]-2,4-dihydro- 4-[(2'-sulfamoylbiphenyl-4-yl)methyl]-3H-1,2,4-triazol-3-one (from Step C) and 2-chlorobenzoic acid (2 equivalents), CDI (2 equiv), and DBU (2 equiv) according to the procedure of Example 51 to give an 88% yield of the desired material as a white solid after flash chromatography, mp 98°-101° C., homogeneous by TLC in 95:5 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 693 (M+1)+.

Sources & evidence

ORD record
ord-8ea58b946d674967a8d3b1be2483678d
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Linked notes

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