2-Chlorobenzoic Acid → 4''-[3-Butyl-5-oxo-1-(2-trifluoromethyl-phenyl)-1,5-dihydro-[1,2,4]triazol-4-ylmethyl]-5-propyl-biphenyl-2-sulfonic acid 2-chloro-benzoylamide

HRID 36268

Reaction equation

HRID 36268 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[C:32]([CH2:34][CH2:35][CH3:36])[CH:31]=[CH:30][C:29]=3[S:37](=[O:40])(=[O:39])[NH2:38])=[CH:24][CH:23]=2)[C:7](=[O:20])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([F:19])([F:18])[F:17])[N:9]=1)[CH2:2][CH2:3][CH3:4].[Cl:41][C:42]1[CH:50]=[CH:49][CH:48]=[CH:47][C:43]=1[C:44](O)=[O:45].C1N=CN(C(N2C=NC=C2)=O)C=1.C1CCN2C(=NCCC2)CC1>>[CH2:1]([C:5]1[N:6]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[C:32]([CH2:34][CH2:35][CH3:36])[CH:31]=[CH:30][C:29]=3[S:37](=[O:40])(=[O:39])[NH:38][C:44](=[O:45])[C:43]3[CH:47]=[CH:48][CH:49]=[CH:50][C:42]=3[Cl:41])=[CH:24][CH:23]=2)[C:7](=[O:20])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([F:19])([F:18])[F:17])[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 199393875-n-butyl-2,4-dihydro-2-[2-(trifluoromethyl)phenyl]-4-[(2'-sulfamoyl-5'-propylbiphenyl-4-yl)methyl]-3H-1,2,4-triazol-3-one

Product 1

HCID 199394094''-[3-Butyl-5-oxo-1-(2-trifluoromethyl-phenyl)-1,5-dihydro-[1,2,4]triazol-4-ylmethyl]-5-propyl-biphenyl-2-sulfonic acid 2-chloro-benzoylamide

Procedure

The title compound was prepared from 5-n-butyl-2,4-dihydro-2-[2-(trifluoromethyl)phenyl]-4-[(2'-sulfamoyl-5'-propylbiphenyl-4-yl)methyl]-3H-1,2,4-triazol-3-one (from Step E) and 2-chlorobenzoic acid (2.0 equivalents), CDI (2.0 equiv), and DBU (2.0 equiv) according to the procedure of Example 51 to give an 86% yield of the desired material as a cream-colored solid after flash chromatography, mp 67°-69° C.; homogeneous by TLC in 9:1 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 711 (M+1)+.

Sources & evidence

ORD record
ord-679a733918234dfba9ee112c29841e81
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Linked notes

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