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

HRID 1676995Notes

Reaction equation

HRID 1676995 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][S:64]([NH2:67])(=[O:66])=[O:65]>>[NH2:67][S:64]([CH2:63][CH2:62][NH:61][S:53]([C:33]1[C:32]2[C:36](=[CH:37][CH:38]=[C:30]([Br:29])[CH:31]=2)[NH:35][C:34]=1[C:48]([NH2:7])=[O:50])(=[O:54])=[O:55])(=[O:66])=[O:65]

Participants

5

Reactant 4

HCID 30215492-Aminoethanesulphonamide monohydrochlorideHCID 6364545Methylamine hydrochlorideHCID 22401482ethyl 5-chloro-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylateHCID 86592455ethyl 3-(chlorosulfonyl)-5-bromo-1-(phenylsulfonyl)-1H-indole-2-carboxylate

Product 1

HCID 103201873-({[2-(Aminosulfonyl)ethyl]amino}sulfonyl)-5-bromo-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-bromo-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylate, and methylamine hydrochloride with 2-aminoethanesulfonamide hydrochloride, the title compound was obtained as a white solid. HRMS (ES) exact mass calculated for C11H13BrN4O5S2Na (M+Na+): 446.9403. Found 446.9404.

Sources & evidence

ORD record
ord-d637191266ae40deb22a697adffc81c8
Source dataset
uspto-grants-2011_08
Patent number
US08008295B2

Reaction notes

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