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

HRID 227499Notes

Reaction equation

ClC1C=C2[C:8](=CC=1)[N:7](S(C1C=CC=CC=1)(=O)=O)[C:6]([C:20]([O:22]CC)=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].[NH:57]1CCOCC1.OC1CNC1>>[OH:22][CH:20]1[CH2:6][N:7]([S:53]([C:33]2[C:32]3[C:36](=[CH:37][CH:38]=[C:30]([I:29])[CH:31]=3)[NH:35][C:34]=2[C:48]([NH2:57])=[O:50])(=[O:54])=[O:55])[CH2:8]1

Participants

Reactant 4

HCID 8083Morpholine

HCID 15142903-Hydroxyazetidine

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

HCID 86601816ethyl 5-iodo-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylate

Product 1

HCID 577562093-[(3-Hydroxyazetidin-1-yl)sulfonyl]-5-iodo-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 morpholine with 3-hydroxyazetidine, the title compound was obtained. Proton NMR for the product was consistent with the titled compound. ESI+MS: 421.88 [M+H]+.

Sources & evidence

ORD record: ord-3a59ebb2ccbb48f7b0368248cc361783
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560546B2

Reaction notes

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