5-Chloro-2-methoxybenzene-1-sulfonyl chloride → 1-(5-chloro-2-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid (4-cyano-phenyl)-amide
Reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2[CH:20]=[C:19]3[C:15]([CH2:16][CH2:17][NH:18]3)=[CH:14][CH:13]=2)=[O:11])=[CH:5][CH:4]=1)#[N:2].[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([O:32][CH3:33])=[C:26]([S:28](Cl)(=[O:30])=[O:29])[CH:27]=1>>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]([C:12]2[CH:20]=[C:19]3[C:15]([CH2:16][CH2:17][N:18]3[S:28]([C:26]3[CH:27]=[C:22]([Cl:21])[CH:23]=[CH:24][C:25]=3[O:32][CH3:33])(=[O:29])=[O:30])=[CH:14][CH:13]=2)=[O:11])=[CH:7][CH:8]=1)#[N:2]Participants
Procedure
1-(5-Chloro-2-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid [4-(1H-tetrazol-5-yl)-phenyl]-amide, MS (ISP), m/e=509.1 (M−H), was prepared in analogy to example 13, steps 1 to 4. Step 1 was performed using 4-amino-benzonitrile and yielded 1H-indole-6-carboxylic acid (4-cyano-phenyl)-amide which was reduced to 2,3-dihydro-1H-indole-6-carboxylic acid (4-cyano-phenyl)-amide in step 2. This was coupled with 5-chloro-2-methoxy benzenesulfonyl chloride in step 3, yielding 1-(5-chloro-2-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid (4-cyano-phenyl)-amide, which was converted to 1-(5-chloro-2-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid [4-(1H-tetrazol-5-yl)-phenyl]-amide by reaction with ammonium azide in step 4.
Sources & evidence
- ORD record
- ord-17040f9a5a8e44e3bce5571e8eaa7ad4
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07713996B2
Reaction notes
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