Benzoic Acid → 4''-[3-(2-Methyl-cyclopropylmethyl)-5-oxo-1-(2-trifluoromethyl-phenyl)-1,5-dihydro-[1,2,4]triazol-4-ylmethyl]-biphenyl-2-sulfonic acid benzoylamide

HRID 36242Notes

Reaction equation

[CH3:1][CH:2]1[CH2:4][CH:3]1[CH2:5][C:6]1[N:7]([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:8](=[O:21])[N:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([F:20])([F:19])[F:18])[N:10]=1.[C:39](O)(=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>>[C:39]([NH:36][S:35]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[C:26]1[CH:25]=[CH:24][C:23]([CH2:22][N:7]2[C:6]([CH2:5][CH:3]3[CH2:4][CH:2]3[CH3:1])=[N:10][N:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:17]([F:18])([F:20])[F:19])[C:8]2=[O:21])=[CH:28][CH:27]=1)(=[O:38])=[O:37])(=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

Reactant 2

HCID 243Benzoic Acid

HCID 10459981HCID 10459981, compound

Product 1

HCID 101007234''-[3-(2-Methyl-cyclopropylmethyl)-5-oxo-1-(2-trifluoromethyl-phenyl)-1,5-dihydro-[1,2,4]triazol-4-ylmethyl]-biphenyl-2-sulfonic acid benzoylamide

Procedure

The title compound was prepared from 2,4-dihydro-5-[(2-methylcyclopropyl)methyl]-4-[(2'-sulfamoylbiphenyl-4-yl)methyl]-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one (from Step G) and benzoic acid according to the procedure of Example 43. The crude material was purified by flash chromatography over silica gel (gradient elution using 0.5-5.0% MeOH/CH2Cl2) to give a 64% of the desired material as a white solid, homogeneous by TLC (5% MeOH/CH2Cl2); mass spectrum (FAB) m/e 647 (M+1)+ ; mp 123°-125° C.

Workup

customThe crude material was purified by flash chromatography over silica gel (gradient elution using 0.5-5.0% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-2bbae08a172a4431bd024c350eac009b
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05411980

Reaction notes

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