4-Methylanthranilic acid → HCID 10110562, compound

HRID 1182238Notes

Reaction equation

HRID 1182238 reaction equation
[C:1]1([C:7]2[NH:8][C:9]3[C:14]([C:15]=2[CH2:16][C:17](O)=[O:18])=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.CN(C)CCCN=C=NCC.[CH3:32][C:33]1[CH:34]=[C:35]([NH2:42])[C:36](=[CH:40][CH:41]=1)[C:37]([OH:39])=[O:38]>ClCCl>[CH3:32][C:33]1[CH:41]=[CH:40][C:36]([C:37]([OH:39])=[O:38])=[C:35]([NH:42][C:17](=[O:18])[CH2:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]=2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:34]=1

Participants

5

Reactant 3

HCID 753164-Methylanthranilic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 3982630(2-phenyl-1H-indol-3-yl)acetic acid

Product 1

HCID 10110562HCID 10110562, compoundYield 20.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Phenyl-3-indole acetic acid (0.166 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.127 g) and 4-methylanthranilic acid (0.100 g) in dichloromethane (20 ml) were refluxed for 48 h under nitrogen. The solvent was then removed and the residue purified using mass spectroscopy directed automated HPLC to afford the title compound (0.053 g). LC/MS TR 3.58 min, MH+ 384.

Workup

  1. customThe solvent was then removed
  2. customthe residue purified

Sources & evidence

ORD record
ord-7b0a70ae73784d6cb5d44831a41e207c
Source dataset
uspto-grants-2007_10
Patent number
US07288564B2

Reaction notes

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