Methylamine hydrochloride → (+/-)-5-Iodo-3-{[methyl(tetrahydro-2H-pyran-2-ylmethyl)amino]sulfonyl}-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.[I: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.[O:60]1[CH2:65][CH2:64][CH2:63][CH2:62][CH:61]1[CH2:66][NH:67][CH3:68]>>[I:29][C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[NH:35][C:34]([C:48]([NH2:7])=[O:50])=[C:33]2[S:53]([N:67]([CH3:68])[CH2:66][CH:61]1[CH2:62][CH2:63][CH2:64][CH2:65][O:60]1)(=[O:54])=[O:55]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-iodo-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylate, and methylamine hydrochloride with (±)-N-(1-tetrahydro-2H-pyran-2-ylmethyl) -N-methylamine, the title compound was obtained. Proton NMR for the product was consistent with the titled compound. ESI+ MS: 477.99 [M+H]+.
Sources & evidence
- ORD record
- ord-75f7300f50cc4b75aaf61f368673d990
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08008295B2
Reaction notes
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