5-formyl-2,4-dimethyl-N-(2-(pyrrolidin-1-yl)ethyl)-1H-pyrrole-3-carboxamide → 2,4-Dimethyl-5-(2-oxo-5-(pyridin-3-ylsulfamoyl)-1,2-dihydroindol-3-ylidenemethyl]-1H-pyrrole-3-carboxylic acid (2-pyrrolidin-1-ylethyl)amide

HRID 1368486Notes

Reaction equation

HRID 1368486 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][S:8]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][C:15](=[O:20])[CH2:14]3)(=[O:10])=[O:9])[CH:2]=1.[N:21]1([CH2:26][CH2:27][NH:28][C:29]([C:31]2[C:35]([CH3:36])=[C:34]([CH:37]=O)[NH:33][C:32]=2[CH3:39])=[O:30])[CH2:25][CH2:24][CH2:23][CH2:22]1>>[N:21]1([CH2:26][CH2:27][NH:28][C:29]([C:31]2[C:35]([CH3:36])=[C:34]([CH:37]=[C:14]3[C:13]4[C:17](=[CH:18][CH:19]=[C:11]([S:8](=[O:10])(=[O:9])[NH:7][C:3]5[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=5)[CH:12]=4)[NH:16][C:15]3=[O:20])[NH:33][C:32]=2[CH3:39])=[O:30])[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

3

Reactant 2

HCID 207617295-formyl-2,4-dimethyl-N-(2-(pyrrolidin-1-yl)ethyl)-1H-pyrrole-3-carboxamideHCID 690525102-Oxo-2,3-dihydro-1H-indole-5-sulfonic acid pyridin-3-ylamide

Product 1

HCID 672819692,4-Dimethyl-5-(2-oxo-5-(pyridin-3-ylsulfamoyl)-1,2-dihydroindol-3-ylidenemethyl]-1H-pyrrole-3-carboxylic acid (2-pyrrolidin-1-ylethyl)amideYield 74%

Procedure

2-Oxo-2,3-dihydro-1H-indole-5-sulfonic acid pyridin-3-ylamide (110 mg, 0.38 mmol) was condensed with 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-pyrrolidin-1-ylethyl)amide (100 mg) to give 150 mg (74%) of the title compound as an orange solid.

Sources & evidence

ORD record
ord-48fe2c83bf90498e83a0a57a0104c486
Source dataset
uspto-grants-2003_06
Patent number
US06573293B2

Reaction notes

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