3-amino-N-(4-ethyl-phenyl)-benzamide → 5-Acetyl-1-ethyl-2-oxo-2,3-dihydro-1H-indole-3-carboxylic acid [3-(4-ethyl-phenylcarbamoyl)-phenyl]-amide

HRID 610063Notes

Reaction equation

HRID 610063 reaction equation
CO[C:3]([CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]3([CH3:19])[O:18]CCO3)[CH:12]=2)[N:7]([CH2:20][CH3:21])[C:6]1=[O:22])=[O:4].[NH2:23][C:24]1[CH:25]=[C:26]([CH:38]=[CH:39][CH:40]=1)[C:27]([NH:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH3:37])=[CH:32][CH:31]=1)=[O:28]>>[CH2:36]([C:33]1[CH:32]=[CH:31][C:30]([NH:29][C:27]([C:26]2[CH:25]=[C:24]([NH:23][C:3]([CH:5]3[C:13]4[C:8](=[CH:9][CH:10]=[C:11]([C:14](=[O:18])[CH3:19])[CH:12]=4)[N:7]([CH2:20][CH3:21])[C:6]3=[O:22])=[O:4])[CH:40]=[CH:39][CH:38]=2)=[O:28])=[CH:35][CH:34]=1)[CH3:37]

Participants

3

Reactant 2

HCID 167883433-amino-N-(4-ethyl-phenyl)-benzamideHCID 538933521-ethyl-5-(2-methyl-[1,3]dioxolan-2-yl)-2-oxo-2,3-dihydro-1H-indole-3-carboxylic acid methyl ester

Product 1

HCID 99563165-Acetyl-1-ethyl-2-oxo-2,3-dihydro-1H-indole-3-carboxylic acid [3-(4-ethyl-phenylcarbamoyl)-phenyl]-amide

Procedure

Prepared as in Example 1 from 1-ethyl-5-(2-methyl-[1,3]dioxolan-2-yl)-2-oxo-2,3-dihydro-1H-indole-3-carboxylic acid methyl ester and 3-amino-N-(4-ethyl-phenyl)-benzamide. Purified by chromatography (chloroform/methanol, 10:1). 1H NMR (DMSO-d6) δ 1.15 (m, 6 H), 2.5 (q, 2 H), 3.85 (q, 2 H), 6.85-8.3 (m, 11 H), 10.0 (s, 1 H), 11.1 (s, 1 H).

Workup

  1. customPurified by chromatography (chloroform/methanol, 10:1)

Sources & evidence

ORD record
ord-c962f4936b104b80af0b9311977a8956
Source dataset
uspto-grants-1999_12
Patent number
US05998463

Reaction notes

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