Methylamine hydrochloride → 3-[({2-[4-(Aminosulfonyl)phenyl]ethyl}amino)sulfonyl]-5-bromo-1H-indole-2-carboxamide
Reaction equation
ClC1C=C2C(=CC=1)[N:7](S(C1C=CC=CC=1)(=O)=O)C(C(OCC)=O)=C2S(Cl)(=O)=O.[Br:29][C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[N:35](S(C1C=CC=CC=1)(=O)=O)[C:34]([C:48]([O:50]CC)=O)=[C:33]2[S:53](Cl)(=[O:55])=[O:54].Cl.CN.Cl.[NH2:61][CH2:62][CH2:63][C:64]1[CH:69]=[CH:68][C:67]([S:70]([NH2:73])(=[O:72])=[O:71])=[CH:66][CH:65]=1>>[NH2:73][S:70]([C:67]1[CH:66]=[CH:65][C:64]([CH2:63][CH2:62][NH:61][S:53]([C:33]2[C:32]3[C:36](=[CH:37][CH:38]=[C:30]([Br:29])[CH:31]=3)[NH:35][C:34]=2[C:48]([NH2:7])=[O:50])(=[O:54])=[O:55])=[CH:69][CH:68]=1)(=[O:71])=[O:72]Participants
5
Reactant 4
Product 1
Procedure
Following the procedures described in Steps D and E of Example 1, replacing in Step D ethyl 5-chloro-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylate with ethyl 5-bromo-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylate, and methylamine hydrochloride with 4-(aminoethyl)benzene-sulfonamide hydrochloride, the title compound was obtained. HRMS (ES) exact mass calculated for C17H18BrN4O5S2 (M+H+): 500.9897. Found 500.9927.
Sources & evidence
- ORD record
- ord-a27b6f0d8b164b45927a897a74dbd526
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08008295B2
Reaction notes
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