2-Chlorobenzoic Acid → 3-n-Butyl-1-[5-(N-n-butylcarbamoyl)-2-(trifluoromethyl)phenyl]-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-1H-pyrazole-5-carbonitrile
Reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[N-]1C=CN=C1.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH2:28]([C:32]1[C:36]([CH2:37][C:38]2[CH:43]=[CH:42][C:41]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=3[S:50](=[O:53])(=[O:52])[NH2:51])=[CH:40][C:39]=2[F:54])=[C:35]([C:55]#[N:56])[N:34]([C:57]2[CH:62]=[C:61]([C:63](=[O:69])[NH:64][CH2:65][CH2:66][CH2:67][CH3:68])[CH:60]=[CH:59][C:58]=2[C:70]([F:73])([F:72])[F:71])[N:33]=1)[CH2:29][CH2:30][CH3:31].C1CCN2C(=NCCC2)CC1>>[CH2:28]([C:32]1[C:36]([CH2:37][C:38]2[CH:43]=[CH:42][C:41]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=3[S:50](=[O:52])(=[O:53])[NH:51][C:4](=[O:6])[C:3]3[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=3[Cl:1])=[CH:40][C:39]=2[F:54])=[C:35]([C:55]#[N:56])[N:34]([C:57]2[CH:62]=[C:61]([C:63](=[O:69])[NH:64][CH2:65][CH2:66][CH2:67][CH3:68])[CH:60]=[CH:59][C:58]=2[C:70]([F:72])([F:71])[F:73])[N:33]=1)[CH2:29][CH2:30][CH3:31]Participants
6
Reactant 5
Product 1
Procedure
Following the procedure of Example 1, Step H, 2-chlorobenzoic acid is converted to its imidazolide with CDI and subsequently reacted with 3-n-butyl-1-[5-(N-n-butylcarbamoyl)-2-(trifluoromethyl)phenyl]-4-[(3-fluoro-2'-sulfamoylbiphenyl-4-yl)methyl]-1H-pyrazole-5-carbonitrile (from Step L) in the presence of DBU to yield the title compound.
Sources & evidence
- ORD record
- ord-5ca51f1c90dc45f3949b6968cd1f9fe3
- Source dataset
- uspto-grants-1993_11
- Patent number
- US05262412
Reaction notes
Loading…