1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Methyl 3-(4-{6-[N'-(4-methoxybenzoyl)-hydrazinocarbonyl]-1H-indol-2-yl}-3,5-dimethyl-phenyl)-propionate

HRID 1513285Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1513285
[CH3:1][O:2][C:3]([CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[NH:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[C:18]([C:23](O)=[O:24])[CH:17]=3)=[C:9]([CH3:26])[CH:8]=1)=[O:4].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH3:48][O:49][C:50]1[CH:59]=[CH:58][C:53]([C:54]([NH:56][NH2:57])=[O:55])=[CH:52][CH:51]=1>C1COCC1>[CH3:48][O:49][C:50]1[CH:51]=[CH:52][C:53]([C:54]([NH:56][NH:57][C:23]([C:18]2[CH:17]=[C:16]3[C:21]([CH:22]=[C:14]([C:10]4[C:11]([CH3:13])=[CH:12][C:7]([CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])=[CH:8][C:9]=4[CH3:26])[NH:15]3)=[CH:20][CH:19]=2)=[O:24])=[O:55])=[CH:58][CH:59]=1

Komponenten

6

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 767924-MethoxybenzohydrazideHCID 669662052-[4-(2-Methoxycarbonylethyl)-2,6-dimethylphenyl]-1H-indole-6-carboxylic acid

Produkt 1

HCID 66966407Methyl 3-(4-{6-[N'-(4-methoxybenzoyl)-hydrazinocarbonyl]-1H-indol-2-yl}-3,5-dimethyl-phenyl)-propionate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a mixture of 2-[4-(2-methoxycarbonylethyl)-2,6-dimethylphenyl]-1H-indole-6-carboxylic acid (200 mg, 570 μmol) and HOBT (85 mg, 630 μmol) in THF (10 mL) was added EDCI (164 mg, 860 μmol) and the solution was stirred at RT for 10 min. Then a solution of 4-methoxybenzoic acid hydrazide (104 mg, 630 μmols) in THF (5 mL) was added and the mixture was stirred at RT for 18 h. The solvent was removed under reduced pressure and the residual material was chromatographed using a 50-90% gradient of heptane/ethyl acetate to give the title compound.

Aufarbeitung

  1. stirringthe mixture was stirred at RT for 18 h
  2. customThe solvent was removed under reduced pressure
  3. customthe residual material was chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-72d2f6701efc4ffd9cdcdc110f3b8d3f
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08217065B2

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