3-(Trifluoromethyl)benzenesulfonyl chloride → 2-Methoxy-4-[3-(3-trifluoromethyl-benzenesulfonylamino)-benzoylamino]-benzoic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:20])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[CH:14]=2)=[CH:7][C:6]=1[O:21][CH3:22])[CH3:2].[F:24][C:25]([F:37])([F:36])[C:26]1[CH:27]=[C:28]([S:32](Cl)(=[O:34])=[O:33])[CH:29]=[CH:30][CH:31]=1>>[CH2:1]([O:3][C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:20])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][S:32]([C:28]3[CH:29]=[CH:30][CH:31]=[C:26]([C:25]([F:24])([F:36])[F:37])[CH:27]=3)(=[O:34])=[O:33])[CH:14]=2)=[CH:7][C:6]=1[O:21][CH3:22])[CH3:2]Participants
3
Procedure
2-Methoxy-4-[3-(3-trifluoromethyl-benzenesulfonylamino)-benzoylamino]-benzoic acid, MS (ISP): m/e=493.3 (M−H), was prepared in analogy to example 1, steps A to D. Step A was performed using 4-amino-2-methoxy-benzoic acid ethyl ester and yielded 2-methoxy-4-(3-nitro-benzoylamino)-benzoic acid ethyl ester. This was reduced to 4-(3-amino-benzoylamino)-2-methoxy-benzoic acid ethyl ester in step B. This was coupled with 3-trifluoromethyl-benzenesulfonyl chloride in step C, yielding 2-methoxy-4-[3-(3-trifluoromethyl-benzenesulfonylamino)-benzoylamino]-benzoic acid ethyl ester, which was hydrolyzed in step D.
Sources & evidence
- ORD record
- ord-96a6d8ced006489098147beb6ea44f0a
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07723538B2
Reaction notes
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