n-(3-Dimethylamino-propyl)-n-methylsulphonyl-p-phenylenediamine → methyl (3Z)-3-[[4-[3-(dimethylamino)propyl-methylsulfonylamino]anilino]-phenylmethylidene]-2-oxo-1H-indole-6-carboxylate

HRID 1883800Notes

Reaction equation

HRID 1883800 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=2)[C:6](=[C:17](OCC)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:5]1=[O:27])(=O)C.[CH3:28][N:29]([CH3:45])[CH2:30][CH2:31][CH2:32][N:33]([S:41]([CH3:44])(=[O:43])=[O:42])[C:34]1[CH:39]=[CH:38][C:37]([NH2:40])=[CH:36][CH:35]=1>>[CH3:45][N:29]([CH3:28])[CH2:30][CH2:31][CH2:32][N:33]([C:34]1[CH:39]=[CH:38][C:37]([NH:40]/[C:17](=[C:6]2\[C:5](=[O:27])[NH:4][C:12]3[C:7]\2=[CH:8][CH:9]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=3)/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:36][CH:35]=1)[S:41]([CH3:44])(=[O:43])=[O:42]

Participants

3

Reactant 2

HCID 23506963n-(3-Dimethylamino-propyl)-n-methylsulphonyl-p-phenylenediamineHCID 666859721-Acetyl-3-(1-ethoxy-1-phenylmethylene)-6-methoxycarbonyl-2-indolinone

Product 1

HCID 178497177methyl (3Z)-3-[[4-[3-(dimethylamino)propyl-methylsulfonylamino]anilino]-phenylmethylidene]-2-oxo-1H-indole-6-carboxylate

Procedure

Prepared from 1-acetyl-3-(1-ethoxy-1-phenylmethylene)-6-methoxycarbonyl-2-indolinone and N-(3-dimethylamino-propyl)-N-methylsulphonyl-p-phenylenediamine Rf value: 0.5 (aluminium oxide, methylene chloride/methanol=30:1) C29H32N4O5S

Sources & evidence

ORD record
ord-2caca4173e4244198dbe195289999001
Source dataset
uspto-grants-2004_07
Patent number
US06762180B1

Reaction notes

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