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

HRID 36248

Reaction equation

HRID 36248 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH2:23]([C:27]1[N:28]([CH2:46][C:47]2[CH:52]=[CH:51][C:50]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=3[S:59](=[O:62])(=[O:61])[NH2:60])=[CH:49][CH:48]=2)[C:29](=[O:45])[N:30]([C:32]2[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][C:33]=2[C:41]([F:44])([F:43])[F:42])[N:31]=1)[CH2:24][CH2:25][CH3:26].C1CCN2C(=NCCC2)CC1>>[CH2:23]([C:27]1[N:28]([CH2:46][C:47]2[CH:52]=[CH:51][C:50]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=3[S:59](=[O:62])(=[O:61])[NH:60][C:4](=[O:6])[C:3]3[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=3[Cl:1])=[CH:49][CH:48]=2)[C:29](=[O:45])[N:30]([C:32]2[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][C:33]=2[C:41]([F:42])([F:44])[F:43])[N:31]=1)[CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 4

HCID 83742-Chlorobenzoic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 104832385-n-Butyl-2,4-dihydro-2-[4-nitro-2-(trifluoromethyl)phenyl]-4-[(2'-sulfamoylbiphenyl-4-yl)methyl]-3H-1,2,4-triazol-3-one

Product 1

HCID 104849864''-[3-Butyl-1-(4-nitro-2-trifluoromethyl-phenyl)-5-oxo-1,5-dihydro-[1,2,4]triazol-4-ylmethyl]-biphenyl-2-sulfonic acid 2-chloro-benzoylamide

Procedure

The title compound was prepared from 2-chlorobenzoic acid (2.0 equivalents), CDI (2.0 equiv), 5-n-butyl-2,4-dihydro-2-(4-nitro-2-trifluoromethyl)phenyl-4-[(2'-sulfamoylbiphenyl-4-yl)methyl]-3H-1,2,4-triazol-3-one (from Step C) (1.0 eq), and DBU (2.0 equiv) according to the procedure of Example 51, to give a 43% yield of the desired material after flash chromatography, as a glassy solid, mp 179°-181° C., homogeneous by TLC in 95:5 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 714 (M+1)+.

Sources & evidence

ORD record
ord-ad5bf4541af44082ad598a21d96c599e
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Linked notes

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