N-(2-Oxoindolin-6-yl)acetamide → N-{3-[3-cyclohexyl-4-(2-morpholin-4-ylethoxy)-benzyl]-2-oxo-2,3-dihydro-1H-indol-6-yl}-acetamide

HRID 2120207Notes

Reaction equation

HRID 2120207 reaction equation
C(NC1C=C2C(CC(=O)N2)=CC=1)(=O)C.C1(C2C=C(C=CC=2OCCN2CCOCC2)C=O)CCCCC1.[CH:38]1([C:44]2[CH:45]=[C:46]([CH:62]=[CH:63][C:64]=2[O:65][CH2:66][CH2:67][N:68]2[CH2:73][CH2:72][O:71][CH2:70][CH2:69]2)[CH:47]=[C:48]2[C:56]3[C:51](=[CH:52][C:53]([NH:57][C:58](=[O:60])[CH3:59])=[CH:54][CH:55]=3)[NH:50][C:49]2=[O:61])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1>>[CH:38]1([C:44]2[CH:45]=[C:46]([CH:62]=[CH:63][C:64]=2[O:65][CH2:66][CH2:67][N:68]2[CH2:69][CH2:70][O:71][CH2:72][CH2:73]2)[CH2:47][CH:48]2[C:56]3[C:51](=[CH:52][C:53]([NH:57][C:58](=[O:60])[CH3:59])=[CH:54][CH:55]=3)[NH:50][C:49]2=[O:61])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1

Participants

4

Reactant 3

HCID 2749839N-(2-Oxoindolin-6-yl)acetamideHCID 53981954N-{3-[3-Cyclohexyl-4-(2-morpholin-4-ylethoxy)-benzylidene]-2-oxo-2,3-dihydro-1H-indol-6-yl}-acetamideHCID 542261743-Cyclohexyl-4-morpholinoethoxybenzaldehyde

Product 1

HCID 23439075N-{3-[3-cyclohexyl-4-(2-morpholin-4-ylethoxy)-benzyl]-2-oxo-2,3-dihydro-1H-indol-6-yl}-acetamideYield 80%

Procedure

6-Acetamido-2-oxindole was condensed with 3-cyclohexyl-4-morpholinoethoxybenzaldehyde using method B to give a mixture of isomers of N-{3-[3-cyclohexyl-4-(2-morpholin-4-ylethoxy)-benzylidene]-2-oxo-2,3-dihydro-1H-indol-6-yl}-acetamide as a mustard yellow solid which was reduced using method E to give 0.04 g (80%) of N-{3-[3-cyclohexyl-4-(2-morpholin-4-ylethoxy)-benzyl]-2-oxo-2,3-dihydro-1H-indol-6-yl}-acetamide as a white solid.

Workup

  1. customto give

Sources & evidence

ORD record
ord-b1f3e734eed041b89ad77e6f2a0758b7
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Reaction notes

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