Potassium Carbonate → 2-[1-(4-chlorobenzyl)-1H-indol-3-yl]-2-oxo-N-(5-oxo-2,5-dihydro-3-thienyl)acetamide

HRID 353475Notes

Reaction equation

HRID 353475 reaction equation
[NH2:1][C:2]1[CH2:6][S:5][C:4](=[O:7])[CH:3]=1.COC1C=C2C(=C(OC)C=1)N(CC1C=CC(Cl)=CC=1)C=C2.C(=O)([O-])[O-].[K+].[K+].[Cl:35][C:36]1[CH:56]=[CH:55][C:39]([CH2:40][N:41]2[C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[C:43]([C:50](=[O:54])[C:51](Cl)=[O:52])=[CH:42]2)=[CH:38][CH:37]=1>COCCOC.O>[Cl:35][C:36]1[CH:56]=[CH:55][C:39]([CH2:40][N:41]2[C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[C:43]([C:50](=[O:54])[C:51]([NH:1][C:2]3[CH2:6][S:5][C:4](=[O:7])[CH:3]=3)=[O:52])=[CH:42]2)=[CH:38][CH:37]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 109804772-(1-(4-chlorobenzyl)-1H-indol-3-yl)-2-oxo-acetyl chlorideHCID 222568845,7-Dimethoxy-1-(4-chlorobenzyl)indoleHCID 235140804-amino-5H-thiophen-2-one

Product 1

HCID 235140422-[1-(4-chlorobenzyl)-1H-indol-3-yl]-2-oxo-N-(5-oxo-2,5-dihydro-3-thienyl)acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A suspension of 4-amino-5H-thiophen-2-one of Preparation 5 (103 mg), powdered potassium carbonate (138 mg) and 2-(1-(4-chlorobenzyl)-1H-indol-3-yl)-2-oxo-acetyl chloride of Example 1 (334 mg) in 1,2-dimethoxyethane (5 ml) is stirred at room temperature for 2 h. After this time the reaction mixture is poured in water (50 ml) and the obtained precipitate is collected by filtration and thoroughly washed with water. The still wet solid is suspended in methanol and stirred for 30′. Filtration followed by drying at 40° C. under vacuum gives 2-[1-(4-chlorobenzyl)-1H-indol-3-yl]-2-oxo-N-(5-oxo-2,5-dihydro-3-thienyl)acetamide (280 mg).

Workup

  1. filtrationthe obtained precipitate is collected by filtration
  2. washthoroughly washed with water
  3. stirringstirred for 30′
  4. filtrationFiltration
  5. customby drying at 40° C. under vacuum

Sources & evidence

ORD record
ord-2b4124f0d6124809b3de884b5fbdbcec
Source dataset
uspto-grants-2004_06
Patent number
US06753342B2

Reaction notes

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