N-methyl-2-oxoindoline-5-sulfonamide → 3-[1-(3-{3-[4-(2-Hydroxy-acetyl)-piperazin-1-yl]-propyl}-4,5,6,7-tetrahydro-1H-indol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid methylamide

HRID 1836143Notes

Reaction equation

HRID 1836143 reaction equation
[OH:1][CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][CH2:13][C:14]2[C:22]3[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=3[NH:16][C:15]=2[CH:23]=O)[CH2:7][CH2:6]1)=[O:4].[CH3:25][NH:26][S:27]([C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[NH:35][C:34](=[O:39])[CH2:33]2)(=[O:29])=[O:28]>>[CH3:25][NH:26][S:27]([C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[NH:35][C:34](=[O:39])/[C:33]/2=[CH:23]\[C:15]1[NH:16][C:17]2[CH2:18][CH2:19][CH2:20][CH2:21][C:22]=2[C:14]=1[CH2:13][CH2:12][CH2:11][N:8]1[CH2:7][CH2:6][N:5]([C:3](=[O:4])[CH2:2][OH:1])[CH2:10][CH2:9]1)(=[O:29])=[O:28]

Participants

3

Reactant 2

HCID 10176909N-methyl-2-oxoindoline-5-sulfonamideHCID 23498835HCID 23498835, compound

Product 1

HCID 442992523-[1-(3-{3-[4-(2-Hydroxy-acetyl)-piperazin-1-yl]-propyl}-4,5,6,7-tetrahydro-1H-indol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid methylamideYield 35.7%

Procedure

3-{3-[4-(2-Hydroxy-acetyl)-piperazin-1-yl]-propyl}-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde (134 mg, 0.3 mmol) was condensed with 5-methylaminosulfonyloxindole (76 Mg, 0.33 mmol) following the procedure used in Example 1 to give 58 mg of the desired product.

Sources & evidence

ORD record
ord-bbb927bab3dc4c9da468c64c51b97f7b
Source dataset
uspto-grants-2004_08
Patent number
US06777417B2

Reaction notes

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