((1,4-Dioxan-2-yl)methyl)(methyl)amine → (+/-)-5-Bromo-3-{[(1,4-dioxan-2-ylmethyl)(methyl)amino]sulfonyl}-1H-indole-2-carboxamide

HRID 1676985Notes

Reaction equation

HRID 1676985 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.[CH3:60][NH:61][CH2:62][CH:63]1[CH2:68][O:67][CH2:66][CH2:65][O:64]1>>[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:61]([CH2:62][CH:63]1[CH2:68][O:67][CH2:66][CH2:65][O:64]1)[CH3:60])(=[O:54])=[O:55]

Participants

5

Reactant 4

HCID 3614772((1,4-Dioxan-2-yl)methyl)(methyl)amineHCID 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 58659663(+/-)-5-Bromo-3-{[(1,4-dioxan-2-ylmethyl)(methyl)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-bromo-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylate, and methylamine hydrochloride with (±)-N-methyl-N-(1,4-dioxan-2-ylmethyl)amine, the title compound was obtained. Proton NMR for the product was consistent with the titled compound. ESI+ MS: 432.2 [M+H]+.

Sources & evidence

ORD record
ord-d7dadee4f240427f95272079259f46f6
Source dataset
uspto-grants-2011_08
Patent number
US08008295B2

Reaction notes

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