N-methyl-2-oxoindoline-5-sulfonamide → 3-[1-{3-[3-(4-Formyl-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 1836141Notes

Reaction equation

HRID 1836141 reaction equation
[CH:1]([N:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][CH2:11][C:12]2[C:20]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[NH:14][C:13]=2[CH:21]=O)[CH2:5][CH2:4]1)=[O:2].[CH3:23][NH:24][S:25]([C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[NH:33][C:32](=[O:37])[CH2:31]2)(=[O:27])=[O:26]>>[CH3:23][NH:24][S:25]([C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[NH:33][C:32](=[O:37])/[C:31]/2=[CH:21]\[C:13]1[NH:14][C:15]2[CH2:16][CH2:17][CH2:18][CH2:19][C:20]=2[C:12]=1[CH2:11][CH2:10][CH2:9][N:6]1[CH2:5][CH2:4][N:3]([CH:1]=[O:2])[CH2:8][CH2:7]1)(=[O:27])=[O:26]

Participants

3

Reactant 2

HCID 10176909N-methyl-2-oxoindoline-5-sulfonamideHCID 23498814HCID 23498814, compound

Product 1

HCID 601047723-[1-{3-[3-(4-Formyl-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 65.5%

Procedure

3-[3-(4-Formylpiperazin-1-yl)-propyl]-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde (61 mg, 0.2 mmol), prepared as described in Step 4 of Example 8, was condensed with 5-methylaminosulfonyloxindole (45 mg, 0.2 mmol) following the procedure used in Example 1. Brown solid precipitated out and purified by flash chromatography, eluting with (dichloromethane: methanol 50/1,35/1,30/1) to give 67 mg of the desired product.

Workup

  1. customBrown solid precipitated out
  2. custompurified by flash chromatography
  3. washeluting with (dichloromethane: methanol 50/1,35/1,30/1)

Sources & evidence

ORD record
ord-076d601068f743fba61a2aa22e81dd8f
Source dataset
uspto-grants-2004_08
Patent number
US06777417B2

Reaction notes

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