Ethyl[(pyridin-3-yl)methyl]amine → 4-Chloro-3-[5-chloro-1-(2,4-dimethoxybenzyl)-3-methyl-2-oxo-2,3-dihydro-1H-indol-3-yl]-N-ethyl-N-(pyridin-3-ylmethyl)benzamide

HRID 1724673Notes

Reaction equation

HRID 1724673 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[C:11]1([CH3:33])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([Cl:20])[CH:18]=2)[N:13]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:23]=2[O:30][CH3:31])[C:12]1=[O:32].[CH2:34]([NH:36][CH2:37][C:38]1[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=1)[CH3:35]>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:36]([CH2:34][CH3:35])[CH2:37][C:38]2[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=2)=[O:7])=[CH:4][C:3]=1[C:11]1([CH3:33])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([Cl:20])[CH:18]=2)[N:13]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:23]=2[O:30][CH3:31])[C:12]1=[O:32]

Participants

3

Reactant 2

HCID 4716480Ethyl[(pyridin-3-yl)methyl]amineHCID 187529834-Chloro-3-[5-chloro-1-(2,4-dimethoxybenzyl)-3-methyl-2-oxoindolin-3-yl]benzoic acid2×

Product 1

HCID 187530044-Chloro-3-[5-chloro-1-(2,4-dimethoxybenzyl)-3-methyl-2-oxo-2,3-dihydro-1H-indol-3-yl]-N-ethyl-N-(pyridin-3-ylmethyl)benzamide

Procedure

4-Chloro-3-[5-chloro-1-(2,4-dimethoxybenzyl)-3-methyl-2-oxoindolin-3-yl]benzoic acid, in the racemic form, is treated with N-ethyl-3-pyridylmethylamine (document WO 01/074775, example 201a) and b)). 4-Chloro-3-[5-chloro-1-(2,4-dimethoxybenzyl)-3-methyl-2-oxoindolin-3-yl]benzoic acid, in the racemic form, is described in the document WO 01/074775, in example 101. After silica chromatography, elution being carried out with a dichloromethane/methanol 90/10 mixture, the expected compound, in the racemic form, is obtained crystallized from methanol (white powder).

Workup

  1. washAfter silica chromatography, elution

Sources & evidence

ORD record
ord-2a8002671e604e149c2ab5f20833f384
Source dataset
uspto-grants-2009_02
Patent number
US07488743B2

Reaction notes

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