Morpholine → 3-(azetidin-1-ylsulfonyl)-5-chloro-1H-indole-2-carboxamide

HRID 227470Notes

Reaction equation

HRID 227470 reaction equation
BrC1C=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.[Cl: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.N1CCC1>>[N:7]1([S:53]([C:33]2[C:32]3[C:36](=[CH:37][CH:38]=[C:30]([Cl:29])[CH:31]=3)[NH:35][C:34]=2[C:48]([NH2:57])=[O:50])(=[O:54])=[O:55])[CH2:8][CH2:9][CH2:10]1

Participants

5

Reactant 4

HCID 8083MorpholineHCID 10422AzetidineHCID 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 100642013-(azetidin-1-ylsulfonyl)-5-chloro-1H-indole-2-carboxamide

Procedure

The titled compound was prepared using the procedures described in Steps B and C of Example 2, followed by the procedure described in Step E of Example 1, replacing in Step B of Example 2 ethyl 5-bromo-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylate with ethyl 5-chloro-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylate, and morpholine with azetidine. Proton NMR for the product was consistent with the titled compound.

Workup

  1. customThe titled compound was prepared

Sources & evidence

ORD record
ord-5512a0cda45f41debcf7343aeb72c196
Source dataset
uspto-grants-2009_07
Patent number
US07560546B2

Reaction notes

Loading…