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)-piperazine-1-carboxylic acid ethyl ester

HRID 1836136Notes

Reaction equation

HRID 1836136 reaction equation
[CH2:1]([O:3][C:4]([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)=[O:5])[CH3:2].[CH3:26][NH:27][S:28]([C:31]1[CH:32]=[C:33]2[C:37](=[CH:38][CH:39]=1)[NH:36][C:35](=[O:40])[CH2:34]2)(=[O:30])=[O:29]>>[CH2:1]([O:3][C:4]([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:34]2\[C:35](=[O:40])[NH:36][C:37]3[C:33]\2=[CH:32][C:31]([S:28](=[O:29])(=[O:30])[NH:27][CH3:26])=[CH:39][CH:38]=3)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 10176909N-methyl-2-oxoindoline-5-sulfonamideHCID 86588562HCID 86588562, compound

Product 1

HCID 235185134-(3-{2-[5-methylsulfamoyl-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-4,5,6,7-tetrahydro-1H-indol-3-yl}-propyl)-piperazine-1-carboxylic acid ethyl esterYield 61.5%

Procedure

4-[3-(2-Formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propyl]-piperazine-1-carboxylic acid ethyl ester (65 mg, 0.1 87 mmol) was condensed with 5-methylaminosulfonyloxindole (43 mg, 1.01 eq.) following the same condition used in Example 1 above. The precipitated solid was purified by flash chromatography, eluting with dichloromethan/methanol (50/1, 40/1, 30/1) to provide 65 mg of the desired product.

Workup

  1. customThe precipitated solid was purified by flash chromatography
  2. washeluting with dichloromethan/methanol (50/1, 40/1, 30/1)

Sources & evidence

ORD record
ord-7d26c565f271451fa2f95c0b667051f8
Source dataset
uspto-grants-2004_08
Patent number
US06777417B2

Reaction notes

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