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

HRID 1836150Notes

Reaction equation

HRID 1836150 reaction equation
[CH:1]([C:3]1[NH:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:11]=1[CH2:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]([OH:24])=[O:23])[CH2:17][CH2:16]1)=O.[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:1]\[C:3]1[NH:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:11]=1[CH2:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]([OH:24])=[O:23])[CH2:17][CH2:16]1)(=[O:29])=[O:28]

Participants

3

Reactant 2

HCID 10176909N-methyl-2-oxoindoline-5-sulfonamideHCID 23498825HCID 23498825, compound

Product 1

HCID 10482445[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 acidYield 80%

Procedure

{(4-[3-(2-Formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propyl]-piperazin-1-yl}-acetic acid (50 mg, 0.15 mmol) was condensed with 5-methylaminosulfonyloxindole (40 mg, 0.15 mmol) following the procedure used in Example 1. The formed solid was purified by flash chromatography, eluting with (dichloromethane: methanol 6:1 followed by 4:1:0.01 acetic acid) to give 65 mg of the desired product.

Workup

  1. customThe formed solid was purified by flash chromatography
  2. washeluting with (dichloromethane: methanol 6:1 followed by 4:1:0.01 acetic acid)

Sources & evidence

ORD record
ord-68438a855cda4467a1c852775eb8018f
Source dataset
uspto-grants-2004_08
Patent number
US06777417B2

Reaction notes

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