2-Aminoethanesulphonamide monohydrochloride → 5-Iodo-3-({[2-(aminosulfonyl)ethyl]amino}sulfonyl)-1H-indole-2-carboxamide

HRID 1676975Notes

Reaction equation

HRID 1676975 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.Cl.[NH2:61][CH2:62][CH2:63][S:64]([NH2:67])(=[O:66])=[O:65]>>[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]([NH:61][CH2:62][CH2:63][S:64]([NH2:67])(=[O:66])=[O:65])(=[O:54])=[O:55]

Participants

5

Reactant 4

HCID 30215492-Aminoethanesulphonamide monohydrochlorideHCID 6364545Methylamine hydrochlorideHCID 22401482ethyl 5-chloro-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylateHCID 86601816ethyl 5-iodo-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylate

Product 1

HCID 586596455-Iodo-3-({[2-(aminosulfonyl)ethyl]amino}sulfonyl)-1H-indole-2-carboxamide

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 2-aminoethanesulfonamide hydrochloride, the title compound was obtained. Proton NMR for the product was consistent with the titled compound. ESI+MS: 473.0 [M+H]+.

Sources & evidence

ORD record
ord-181179f5374f4b359aba3aa537bd1567
Source dataset
uspto-grants-2011_08
Patent number
US08008295B2

Reaction notes

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