Cyclopropylamine → 5-bromo-3-[(cyclopropylamino)sulfonyl]-1H-Indole-2-carboxamide

HRID 1677015Notes

Reaction equation

ClC1C=C2[C:8](=[CH:9][CH:10]=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.C1([NH2:63])CC1>>[Br:29][C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[NH:35][C:34]([C:48]([NH2:63])=[O:50])=[C:33]2[S:53]([NH:7][CH:8]1[CH2:9][CH2:10]1)(=[O:54])=[O:55]

Participants

Reactant 4

HCID 69828Cyclopropylamine

HCID 6364545Methylamine hydrochloride

HCID 22401482ethyl 5-chloro-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylate

HCID 86592455ethyl 3-(chlorosulfonyl)-5-bromo-1-(phenylsulfonyl)-1H-indole-2-carboxylate

Product 1

HCID 100439165-bromo-3-[(cyclopropylamino)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-bromo-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylate, and methylamine hydrochloride with cyclopropylamine, the title compound was obtained. Proton NMR for the product was consistent with the titled compound. ESI+ MS: 458.16 [M+H]+.

Sources & evidence

ORD record: ord-45a3c3806b0543d7a76a1d3948039828
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008295B2

Reaction notes

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