HCID 23498835, compound → 5-Ethanesulfonyl-3-[1-(3-{3-[4-(2-hydroxyacetyl)-piperazin-1-yl]-propyl}-4,5,6,7-tetrahydro-1h-indol-2-yl)-meth-(z)-ylidene]-1,3-dihydro-indol-2-one

HRID 1836144Notes

Reaction equation

HRID 1836144 reaction equation
[OH:1][CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][CH2:13][C:14]2[C:22]3[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=3[NH:16][C:15]=2[CH:23]=O)[CH2:7][CH2:6]1)=[O:4].[CH2:25]([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])[CH3:26]>>[CH2:25]([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:23]\[C:15]1[NH:16][C:17]2[CH2:18][CH2:19][CH2:20][CH2:21][C:22]=2[C:14]=1[CH2:13][CH2:12][CH2:11][N:8]1[CH2:9][CH2:10][N:5]([C:3](=[O:4])[CH2:2][OH:1])[CH2:6][CH2:7]1)(=[O:28])=[O:29])[CH3:26]

Participants

3

Reactant 2

HCID 23498835HCID 23498835, compoundHCID 23498854HCID 23498854, compound

Product 1

HCID 442992335-Ethanesulfonyl-3-[1-(3-{3-[4-(2-hydroxyacetyl)-piperazin-1-yl]-propyl}-4,5,6,7-tetrahydro-1h-indol-2-yl)-meth-(z)-ylidene]-1,3-dihydro-indol-2-oneYield 28.4%

Procedure

3-{3-[4-(2-Hydroxy-acetyl)-piperazin-1-yl]-propyl}-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde (134 mg, 0.3 mmol), prepared as described in Example 13, was condensed with 5-ethylsulfonyloxindole (102 mg, 72% pure) following the procedure used in Example 1. Dark solid was precipitated out and purified by flash chromatography, eluting with (dichloromethane/methanol 10/1) to give 46 mg of the desired product.

Workup

  1. customDark solid was precipitated out
  2. custompurified by flash chromatography
  3. washeluting with (dichloromethane/methanol 10/1)

Sources & evidence

ORD record
ord-1d04c1479ec0410783b5272d099b13cb
Source dataset
uspto-grants-2004_08
Patent number
US06777417B2

Reaction notes

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