Dimethylamine → 3-[(Dimethylamino)sulfonyl]-5-methoxy-1H-indole-2-carboxamide

HRID 1676976Notes

Reaction equation

HRID 1676976 reaction equation
ClC1C=C2[C:8](=CC=1)[N:7](S(C1C=CC=CC=1)(=O)=O)[C:6](C(OCC)=O)=C2S(Cl)(=O)=O.Cl[S:30]([C:33]1[C:41]2[C:36](=[CH:37][CH:38]=[C:39]([O:42][CH3:43])[CH:40]=2)[N:35](S(C2C=CC=CC=2)(=O)=O)[C:34]=1[C:53]([O:55]CC)=O)(=[O:32])=[O:31].Cl.CN.C[NH:62]C>O1CCCC1.C(N(CC)CC)C>[CH3:6][N:7]([CH3:8])[S:30]([C:33]1[C:41]2[C:36](=[CH:37][CH:38]=[C:39]([O:42][CH3:43])[CH:40]=2)[NH:35][C:34]=1[C:53]([NH2:62])=[O:55])(=[O:32])=[O:31]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 6364545Methylamine hydrochlorideHCID 22401482ethyl 5-chloro-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylateHCID 86601813HCID 86601813, compound

Product 1

HCID 104699013-[(Dimethylamino)sulfonyl]-5-methoxy-1H-indole-2-carboxamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

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 3-(chlorosulfonyl)-5-methoxy-1-(phenylsulfonyl)-1H-indole-2-carboxylate, and methylamine hydrochloride with dimethylamine 2.0 M solution in tetrahydrofuran, and omitting triethylamine from the reaction mixture, the title compound was obtained. ESI+MS: 298.2 [M+H]+.

Sources & evidence

ORD record
ord-8ebeb4dfa5c34f8382fa0e18d0295369
Source dataset
uspto-grants-2011_08
Patent number
US08008295B2

Reaction notes

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