3-Aminobenzanilide → 5-Cyclopentanecarbonyl-1-ethyl-2-oxo-2,3-dihydro-1H-indole-3-carboxylic acid (3-phenylcarbamoyl-phenyl)-amide

HRID 610072

Reaction equation

HRID 610072 reaction equation
C([O:3][C:4]([CH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]3([CH:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)OCC[O:16]3)[CH:13]=2)[N:8]([CH2:25][CH3:26])[C:7]1=[O:27])=O)C.[NH2:28][C:29]1[CH:30]=[C:31]([CH:41]=[CH:42][CH:43]=1)[C:32]([NH:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:33]>>[C:35]1([NH:34][C:32]([C:31]2[CH:30]=[C:29]([NH:28][C:4]([CH:6]3[C:14]4[C:9](=[CH:10][CH:11]=[C:12]([C:15]([CH:20]5[CH2:21][CH2:22][CH2:23][CH2:24]5)=[O:16])[CH:13]=4)[N:8]([CH2:25][CH3:26])[C:7]3=[O:27])=[O:3])[CH:43]=[CH:42][CH:41]=2)=[O:33])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

3

Reactant 2

HCID 843473-AminobenzanilideHCID 542951295-(2-cyclopentyl-[1,3]dioxolan-2-yl)-1-ethyl-2-oxo-2,3-dihydro-1H-indole-3-carboxylic acid ethyl ester

Product 1

HCID 539665515-Cyclopentanecarbonyl-1-ethyl-2-oxo-2,3-dihydro-1H-indole-3-carboxylic acid (3-phenylcarbamoyl-phenyl)-amide

Procedure

Prepared as in Example 1 from 5-(2-cyclopentyl-[1,3]dioxolan-2-yl)-1-ethyl-2-oxo-2,3-dihydro-1H-indole-3-carboxylic acid ethyl ester and 3-amino-N-phenyl-benzamide. Purified by flash-chromatography (hexanes/acetone, 1:1) followed by trituration in ethyl acetate. mp 208-213° C.

Workup

  1. customPurified by flash-chromatography (hexanes/acetone, 1:1)

Sources & evidence

ORD record
ord-e65b1840a76b4222a87124dfa55b895c
Source dataset
uspto-grants-1999_12
Patent number
US05998463

Linked notes

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