5-formyl-2,4-dimethyl-N-(2-(pyrrolidin-1-yl)ethyl)-1H-pyrrole-3-carboxamide → 2,4-Dimethyl-5-(2-oxo-6-Pyridin-3-yl-1,2-Dihydroindol-3-Ylidenemethyl)-1H-Pyrrole-3-Carboxylic Acid (2-Pyrrolidin-1-Ylethyl) Amide

HRID 1008179Notes

Reaction equation

HRID 1008179 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:15]=[C:14]3[C:10]([CH2:11][C:12](=[O:16])[NH:13]3)=[CH:9][CH:8]=2)[CH:2]=1.[N:17]1([CH2:22][CH2:23][NH:24][C:25]([C:27]2[C:31]([CH3:32])=[C:30]([CH:33]=O)[NH:29][C:28]=2[CH3:35])=[O:26])[CH2:21][CH2:20][CH2:19][CH2:18]1>>[N:17]1([CH2:22][CH2:23][NH:24][C:25]([C:27]2[C:31]([CH3:32])=[C:30]([CH:33]=[C:11]3[C:10]4[C:14](=[CH:15][C:7]([C:3]5[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=5)=[CH:8][CH:9]=4)[NH:13][C:12]3=[O:16])[NH:29][C:28]=2[CH3:35])=[O:26])[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

3

Reactant 2

HCID 207617295-formyl-2,4-dimethyl-N-(2-(pyrrolidin-1-yl)ethyl)-1H-pyrrole-3-carboxamideHCID 219155796-Pyridin-3-yl-1,3-dihydro-indol-2-one

Product 1

HCID 672818472,4-Dimethyl-5-(2-oxo-6-Pyridin-3-yl-1,2-Dihydroindol-3-Ylidenemethyl)-1H-Pyrrole-3-Carboxylic Acid (2-Pyrrolidin-1-Ylethyl) AmideYield 71%

Procedure

6-Pyridin-3-yl-1,3-dihydroindol-2-one (60 mg, 0.28 mmol) was condensed with 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-pyrrolidin-1-ylethyl)amide (75 mg) to give 90 mg (71%) of the title compound as a light orange solid.

Sources & evidence

ORD record
ord-155e7636d85c4feba153f0a365e3f3d2
Source dataset
uspto-grants-2004_09
Patent number
US06797725B2

Reaction notes

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