5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (3-diethylamino-propyl)-amide → 3-[4-(3-Diethylaminopropylcarbamoyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-2-oxo-2,3-dihydro-1H-indole-4-carboxylic acid (3-chloro-4-methoxyphenyl)amide

HRID 1008184Notes

Reaction equation

HRID 1008184 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]([C:13]2[C:14]3[CH2:15][C:16](=[O:22])[NH:17][C:18]=3[CH:19]=[CH:20][CH:21]=2)=[O:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH2:23]([N:25]([CH2:41][CH3:42])[CH2:26][CH2:27][CH2:28][NH:29][C:30]([C:32]1[C:36]([CH3:37])=[C:35]([CH:38]=O)[NH:34][C:33]=1[CH3:40])=[O:31])[CH3:24]>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]([C:13]2[C:14]3[C:15](=[CH:38][C:35]4[NH:34][C:33]([CH3:40])=[C:32]([C:30](=[O:31])[NH:29][CH2:28][CH2:27][CH2:26][N:25]([CH2:41][CH3:42])[CH2:23][CH3:24])[C:36]=4[CH3:37])[C:16](=[O:22])[NH:17][C:18]=3[CH:19]=[CH:20][CH:21]=2)=[O:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

3

Reactant 2

HCID 207617995-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (3-diethylamino-propyl)-amideHCID 701606642-Oxo-2,3-dihydro-1H-indole-4-carboxylic acid (3-chloro-4-methoxyphenyl)amide

Product 1

HCID 672816483-[4-(3-Diethylaminopropylcarbamoyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-2-oxo-2,3-dihydro-1H-indole-4-carboxylic acid (3-chloro-4-methoxyphenyl)amideYield 93.1%

Procedure

2-Oxo-2,3-dihydro-1H-indole-4-carboxylic acid (3-chloro-4-methoxyphenyl)amide (1 g, 3.16 mmol) was condensed with 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (3-diethylaminopropyl)amide (1 g, 3.58 mmol) to give 1.7 g (85%) of the title compound as a yellow-orange solid.

Sources & evidence

ORD record
ord-b9f709fbe21a4efa95419ead5a22b8c3
Source dataset
uspto-grants-2004_09
Patent number
US06797725B2

Reaction notes

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