2-Chlorobenzoic Acid → 3-n-Butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-1-[5-nitro-2-(trifluoromethyl)phenyl]-1H-pyrazole-5-carbonitrile

HRID 257586Notes

Reaction equation

HRID 257586 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.[CH2:16]([C:20]1[C:24]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[S:38](=[O:41])(=[O:40])[NH2:39])=[CH:28][C:27]=2[F:42])=[C:23]([C:43]#[N:44])[N:22]([C:45]2[CH:50]=[C:49]([N+:51]([O-:53])=[O:52])[CH:48]=[CH:47][C:46]=2[C:54]([F:57])([F:56])[F:55])[N:21]=1)[CH2:17][CH2:18][CH3:19].C1CCN2C(=NCCC2)CC1>>[CH2:16]([C:20]1[C:24]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[S:38](=[O:40])(=[O:41])[NH:39][C:4](=[O:6])[C:3]3[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=3[Cl:1])=[CH:28][C:27]=2[F:42])=[C:23]([C:43]#[N:44])[N:22]([C:45]2[CH:50]=[C:49]([N+:51]([O-:53])=[O:52])[CH:48]=[CH:47][C:46]=2[C:54]([F:56])([F:55])[F:57])[N:21]=1)[CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 4

HCID 83742-Chlorobenzoic AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 3386966ImidazolateHCID 197831703-n-Butyl-4-[(3-fluoro-2'-sulfamoylbiphenyl-4-yl)methyl]-1-[5-nitro-2-(trifluoromethyl)phenyl]-1H-pyrazole-5-carbonitrile

Product 1

HCID 197831933-n-Butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-1-[5-nitro-2-(trifluoromethyl)phenyl]-1H-pyrazole-5-carbonitrile

Procedure

By the method of Example 1, Step H, 2-chlorobenzoic acid is converted to its imidazolide and reacted with 3-n-butyl-4-[(3-fluoro-2'-sulfamoylbiphenyl-4-yl)methyl]-1-[5-nitro-2-(trifluoromethyl)phenyl]-1H-pyrazole-5-carbonitrile (from Step B) in the presence of DBU to give the title compound.

Sources & evidence

ORD record
ord-895d241d23a044e7a9f08856d0d408e9
Source dataset
uspto-grants-1993_11
Patent number
US05262412

Reaction notes

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