N-methyl-2-oxoindoline-5-sulfonamide → HCID 44299325, compound

HRID 1836125Notes

Reaction equation

HRID 1836125 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][C:11]2[C:19]3[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=3[NH:13][C:12]=2[CH:20]=O)[CH2:4][CH2:3]1.[CH3:22][NH:23][S:24]([C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[NH:32][C:31](=[O:36])[CH2:30]2)(=[O:26])=[O:25]>>[CH3:22][NH:23][S:24]([C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[NH:32][C:31](=[O:36])/[C:30]/2=[CH:20]\[C:12]1[NH:13][C:14]2[CH2:15][CH2:16][CH2:17][CH2:18][C:19]=2[C:11]=1[CH2:10][CH2:9][CH2:8][N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]1)(=[O:26])=[O:25]

Participants

3

Reactant 2

HCID 10176909N-methyl-2-oxoindoline-5-sulfonamideHCID 225711323-[3-(4-Methylpiperazin-1-yl)-propyl]-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde

Product 1

HCID 44299325HCID 44299325, compoundYield 47%

Procedure

3-[3-(4-Methyl-piperazin-1-yl)-propyl]-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde (87 mg, 0.3 mmol) was condensed with 5-methylaminosulfonyloxindole (68 mg, 0.3 mmol) following the same procedure used in Example 1, step 5 above. No solid precipitated out. The reaction solution was rotary evaporated and purified by flash chromatography and eluting with (dichloromethane: methanol 13/1, 10/1, 8/1) to give (70 mg, 47% yield) of 3-[1-{3-[3-(4-methyl-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.

Workup

  1. customNo solid precipitated out
  2. customThe reaction solution was rotary evaporated
  3. custompurified by flash chromatography
  4. washeluting with (dichloromethane: methanol 13/1, 10/1, 8/1)

Sources & evidence

ORD record
ord-fdb8a0d4e1c447bc8c3a046e0b37c377
Source dataset
uspto-grants-2004_08
Patent number
US06777417B2

Reaction notes

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