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N,N-Dimethylethylenediamine → tert-butyl N-[(4aR*,6R*,8aR*)-3-cyano-6-[({[2-(dimethylamino)ethyl]carbamoyl}(propyl)amino)carbonyl]-8-methyl-4H,4aH,5H,6H,7H,8H,8aH,9H-thieno[3,2-g]quinolin-2-yl]-N-methylcarbamate

HRID 2280213
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2280213
[C:1]([O:5][C:6]([N:8]([CH3:43])[C:9]1[S:21][C:20]2[CH2:19][C@@H:18]3[C@H:13]([CH2:14][C@@H:15]([C:23]([N:25]([CH2:38][CH2:39][CH3:40])[C:26](=O)[O:27]C4C=CC([N+]([O-])=O)=CC=4)=[O:24])[CH2:16][N:17]3[CH3:22])[CH2:12][C:11]=2[C:10]=1[C:41]#[N:42])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:44][N:45]([CH3:49])[CH2:46][CH2:47][NH2:48]>O1CCCC1>[C:41]([C:10]1[C:11]2[CH2:12][C@@H:13]3[C@@H:18]([CH2:19][C:20]=2[S:21][C:9]=1[N:8]([CH3:43])[C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[N:17]([CH3:22])[CH2:16][C@H:15]([C:23]([N:25]([C:26](=[O:27])[NH:48][CH2:47][CH2:46][N:45]([CH3:49])[CH3:44])[CH2:38][CH2:39][CH3:40])=[O:24])[CH2:14]3)#[N:42]
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Komponenten

4

Edukt 2

HCID 66053N,N-DimethylethylenediamineHCID 867310284-nitrophenyl N-{[(4aR*,6R*,8aR*)-2-{[(tert-butoxy)carbonyl](methyl)amino}-3-cyano-8-methyl-4H,4aH,5H,6H,7H,8H,8aH,9H-thieno[3,2-g]quinolin-6-yl]carbonyl}-N-propylcarbamate

Produkt 1

HCID 86731029tert-butyl N-[(4aR*,6R*,8aR*)-3-cyano-6-[({[2-(dimethylamino)ethyl]carbamoyl}(propyl)amino)carbonyl]-8-methyl-4H,4aH,5H,6H,7H,8H,8aH,9H-thieno[3,2-g]quinolin-2-yl]-N-methylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

To a mixture of 4-nitrophenyl N-{[(4aR*,6R*,8aR*)-2-{[(tert-butoxy)carbonyl](methyl)amino}-3-cyano-8-methyl-4H,4aH,5H,6H,7H,8H,8aH,9H-thieno[3,2-g]-quinolin-6-yl]carbonyl}-N-propylcarbamate (200 mg) and tetrahydrofuran (3 mL) was added N,N-dimethyl ethylenediamine (0.071 mL) while stirring at room temperature, and the mixture was stirred at the same temperature for 22 hours. The reaction mixture was concentrated under reduced pressure. The residue was purified by aminopropyl silica gel column chromatography (eluent: 0%-5% methanol/ethyl acetate, gradient elution) to give tert-butyl N-[(4aR*,6R*,8aR*)-3-cyano-6-[({[2-(dimethylamino)ethyl]-carbamoyl}(propyl)amino)carbonyl]-8-methyl-4H,4aH,5H,6H,7H,8H,8 aH,9H-thieno-[3,2-g]quinolin-2-yl]-N-methylcarbamate (160 mg).

Aufarbeitung

  1. stirringthe mixture was stirred at the same temperature for 22 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified by aminopropyl silica gel column chromatography (eluent: 0%-5% methanol/ethyl acetate, gradient elution)

Quellen und Nachweise

ORD-Eintrag
ord-90ab41bf0ab94588906c36698cd58ad0
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09138434B2

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