N-methyl-2-oxoindoline-5-sulfonamide → [4-(3-{2-[5-Methylsulfamoyl-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-4,5,6,7-tetrahydro-1H-indol-3-yl}-propyl)-piperazin-1-yl]-acetic acid ethyl ester

HRID 1836148Notes

Reaction equation

HRID 1836148 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH2:14][C:15]2[C:23]3[CH2:22][CH2:21][CH2:20][CH2:19][C:18]=3[NH:17][C:16]=2[CH:24]=O)[CH2:8][CH2:7]1)[CH3:2].[CH3:27][NH:28][S:29]([C:32]1[CH:33]=[C:34]2[C:38](=[CH:39][CH:40]=1)[NH:37][C:36](=[O:41])[CH2:35]2)(=[O:31])=[O:30]>>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH2:14][C:15]2[C:23]3[CH2:22][CH2:21][CH2:20][CH2:19][C:18]=3[NH:17][C:16]=2/[CH:24]=[C:35]2\[C:36](=[O:41])[NH:37][C:38]3[C:34]\2=[CH:33][C:32]([S:29](=[O:31])(=[O:30])[NH:28][CH3:27])=[CH:40][CH:39]=3)[CH2:8][CH2:7]1)[CH3:2]

Participants

3

Reactant 2

HCID 10176909N-methyl-2-oxoindoline-5-sulfonamideHCID 86588564(4-[3-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propyl]-piperazin-1-yl}-acetic acid ethyl ester

Product 1

HCID 23518511[4-(3-{2-[5-Methylsulfamoyl-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-4,5,6,7-tetrahydro-1H-indol-3-yl}-propyl)-piperazin-1-yl]-acetic acid ethyl ester

Procedure

{(4-[3-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propyl]-piperazin-1-yl}-acetic acid ethyl ester (60 mg, 0.1 73 mmol) was condensed with 5-methylaminosulfonyloxindole (45 mg, 0.1 9 mmol, 1.1 eq.) following the procedure used in Example 1 above. The reaction mixture was purified by flash chromatography (dichloromethane/methanol 10/1) to give the desired product.

Workup

  1. customThe reaction mixture was purified by flash chromatography (dichloromethane/methanol 10/1)

Sources & evidence

ORD record
ord-25edbaacec5e4b9fb53560d262e84c40
Source dataset
uspto-grants-2004_08
Patent number
US06777417B2

Reaction notes

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