Cycloheptanecarboxylic acid → 4''-[3-Butyl-5-oxo-1-(2-trifluoromethyl-phenyl)-1,5-dihydro-[1,2,4]triazol-4-ylmethyl]-biphenyl-2-sulfonic acid cycloheptanecarbonyl-amide
Reaction equation
[CH:1]1([C:8]([OH:10])=O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH2:23]([C:27]1[N:28]([CH2:43][C:44]2[CH:49]=[CH:48][C:47]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=3[S:56](=[O:59])(=[O:58])[NH2:57])=[CH:46][CH:45]=2)[C:29](=[O:42])[N:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[C:38]([F:41])([F:40])[F:39])[N:31]=1)[CH2:24][CH2:25][CH3:26].C1CCN2C(=NCCC2)CC1>>[CH2:23]([C:27]1[N:28]([CH2:43][C:44]2[CH:49]=[CH:48][C:47]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=3[S:56](=[O:59])(=[O:58])[NH:57][C:8]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]3)=[O:10])=[CH:46][CH:45]=2)[C:29](=[O:42])[N:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[C:38]([F:41])([F:40])[F:39])[N:31]=1)[CH2:24][CH2:25][CH3:26]Participants
5
Reactant 4
Product 1
Procedure
The title compound was prepared from cycloheptanecarboxylic acid (2.0 equivalents), CDI (2.0 equivalents), 5-n-butyl-2,4-dihydro-4-[(2'-sulfamoylbiphenyl-4-yl)methyl]-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one (from Example 16, Step C) (1.0 equivalent), and DBU (2.0 equivalents) according to the procedure of Example 7, to give a 69% yield of the desired material after flash chromatography, as a glassy solid, mp 146°-149° C., homogeneous by TLC in 95:5 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 655 (M+1)+.
Sources & evidence
- ORD record
- ord-79511a320cca4bc2aa3059a832f1b8bf
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05411980
Reaction notes
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