1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)-N-(3-methoxyphenethyl)piperidine-4-carboxamide

HRID 83622

Reaktionsgleichung

Reaktionsgleichung von HRID 83622
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([C:24](O)=[O:25])[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.[CH3:50][O:51][C:52]1[CH:53]=[C:54]([CH2:58][CH2:59][NH2:60])[CH:55]=[CH:56][CH:57]=1.CCN(C(C)C)C(C)C>C(Cl)Cl.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([C:24]([NH:60][CH2:59][CH2:58][C:54]3[CH:55]=[CH:56][CH:57]=[C:52]([O:51][CH3:50])[CH:53]=3)=[O:25])[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1

Komponenten

9

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 748663-MethoxyphenethylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 573857961-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid

Produkt 1

HCID 665712771-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)-N-(3-methoxyphenethyl)piperidine-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (100 mg, 0.252 mmol), 1-hydroxybenzotriazole (51.1 mg, 0.378 mmol), and EDCI (72.5 mg, 0.378 mmol) were dissolved in 2.0 mL of DCM. The reaction was allowed to stir at room temperature for 10 minutes before 2-(3-methoxyphenyl)ethanamine (0.056 ml, 0.378 mmol) and Hunig's Base (0.066 ml, 0.378 mmol) were added as a 1.0 mL DCM solution. The reaction was allowed to stir overnight. The reaction was diluted with water and ethyl acetate. The organic phase was washed with 1N HCl, saturated sodium bicarbonate, and brine. The organic phase was dried over magnesium sulfate, filtered, and concentrated. The crude material was triturated with ethyl acetate to obtain product as a white solid. (Yield: 89 mg, white solid)

Aufarbeitung

  1. washThe organic phase was washed with 1N HCl, saturated sodium bicarbonate, and brine
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was triturated with ethyl acetate
  6. customto obtain product as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-7b0e70d032224d87ab12c94bc19d265a
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846684B2

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