2-Chlorobenzoic Acid → 5-n-Butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-2,4-dihydro-2-[5-nitro-2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one
Reaction equation
[CH2:1]([C:5]1[N:6]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[S:37](=[O:40])(=[O:39])[NH2:38])=[CH:27][C:26]=2[F:41])[C:7](=[O:23])[N:8]([C:10]2[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:11]=2[C:19]([F:22])([F:21])[F:20])[N:9]=1)[CH2:2][CH2:3][CH3:4].[Cl:42][C:43]1[CH:51]=[CH:50][CH:49]=[CH:48][C:44]=1[C:45](O)=[O:46].C1N=CN(C(N2C=NC=C2)=O)C=1.C1CCN2C(=NCCC2)CC1>>[CH2:1]([C:5]1[N:6]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[S:37](=[O:40])(=[O:39])[NH:38][C:45](=[O:46])[C:44]3[CH:48]=[CH:49][CH:50]=[CH:51][C:43]=3[Cl:42])=[CH:27][C:26]=2[F:41])[C:7](=[O:23])[N:8]([C:10]2[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:11]=2[C:19]([F:21])([F:20])[F:22])[N:9]=1)[CH2:2][CH2:3][CH3:4]Participants
5
Reactant 4
Product 1
Procedure
By the procedure of Example 51, 5-n-butyl-2,4-dihydro-4-[(3-fluoro-2'-sulfamoylbiphenyl-4-yl)methyl]-2-[5-nitro-2-(trifluoromethyl)-phenyl]-3H-1,2,4-triazol-3-one (from Step E) was reacted with 2-chlorobenzoic acid (3 equivalents), CDI (3 equiv), and DBU (3 equiv). Flash chromatography of the crude product on silica gel afforded an 86% yield of the title compound as a foam; homogeneous by TLC (95:5 CH2Cl2 --MeOH); mass spectrum (FAB) m/e 732 (M+1)+.
Sources & evidence
- ORD record
- ord-a3ba6739d1484bd6bf54e1da27d3fd77
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05411980
Reaction notes
Loading…