Morpholine → 5-Bromo-3-({4-[2-(dimethylamino)ethyl]-5-oxo-1,4-diazepan-1-yl}sulfonyl)-1H-indole-2-carboxamide

HRID 227473Notes

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.C(O)(=O)C(O)=O.[CH3:69][N:70]([CH3:81])[CH2:71][CH2:72][N:73]1[C:79](=[O:80])[CH2:78][CH2:77][NH:76][CH2:75][CH2:74]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:76]1[CH2:77][CH2:78][C:79](=[O:80])[N:73]([CH2:72][CH2:71][N:70]([CH3:81])[CH3:69])[CH2:74][CH2:75]1)(=[O:54])=[O:55]

Participants

Reactant 4

HCID 8083Morpholine

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

HCID 68445140CID 68445140

HCID 86592455ethyl 3-(chlorosulfonyl)-5-bromo-1-(phenylsulfonyl)-1H-indole-2-carboxylate

Product 1

HCID 103906855-Bromo-3-({4-[2-(dimethylamino)ethyl]-5-oxo-1,4-diazepan-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 4-[2-(dimethylamino)ethyl]-1,4-diazepan-5-one oxalate, the title compound was obtained as a white solid. HRMS (ES) exact mass calculated for C18H25BrN5O4S (M+H+): 486.0805. Found 486.0801.

Sources & evidence

ORD record: ord-d466211e217a4cc581432b0f04e277fa
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560546B2

Reaction notes

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