Morpholine → 5-Bromo-3-[(3-oxopiperazin-1-yl)sulfonyl]-1H-indole-2-carboxamide

HRID 227474Notes

Reaction equation

HRID 227474 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].N1CCOCC1.FC(F)(F)C(O)=O.[NH:70]1[CH2:75][CH2:74][NH:73][CH2:72][C:71]1=[O:76]>>[Br: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:73]1[CH2:74][CH2:75][NH:70][C:71](=[O:76])[CH2:72]1)(=[O:54])=[O:55]

Participants

5

Reactant 4

HCID 8083MorpholineHCID 22401482ethyl 5-chloro-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylateHCID 67358098Piperazin-2-one 2,2,2-trifluoroacetateHCID 86592455ethyl 3-(chlorosulfonyl)-5-bromo-1-(phenylsulfonyl)-1H-indole-2-carboxylate

Product 1

HCID 100465845-Bromo-3-[(3-oxopiperazin-1-yl)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 morpholine with piperazin-2-one trifluoroacetate, the title compound was obtained after purification by preparative reversed phase HPLC. Proton NMR for the product was consistent with the titled compound. ESI+MS: 402.1 [M+H]+.

Sources & evidence

ORD record
ord-4588c372e8ea45f3afef257e7f95974a
Source dataset
uspto-grants-2009_07
Patent number
US07560546B2

Reaction notes

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