1-Pyrrolidineethanamine → HCID 86732796, Verbindung

HRID 525928Notizen

Reaktionsgleichung

[Cl:1][C:2]1[C:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[C:10]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:37])[C:5]([C:34](O)=[O:35])=[N:6][N:7]2[CH2:32][CH3:33].C(N(CC)CC)C.ClC(OCC(C)C)=O.[N:53]1([CH2:58][CH2:59][NH2:60])[CH2:57][CH2:56][CH2:55][CH2:54]1>O1CCCC1>[Cl:1][C:2]1[C:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[C:10]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:37])[C:5]([C:34]([NH:60][CH2:59][CH2:58][N:53]1[CH2:57][CH2:56][CH2:55][CH2:54]1)=[O:35])=[N:6][N:7]2[CH2:32][CH3:33]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a suspension of 5-chloro-1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydrocinnoline-3-carboxylic acid (3 g, 5.71 mmol) in tetrahydrofuran (THF) (25 mL) was added triethylamine (0.876 mL, 6.29 mmol), followed by isobutyl chloroformate (0.826 mL, 6.29 mmol). The reaction mixture was stirred at 0° C. for 30 min. 2-(Pyrrolidin-1-yl)ethanamine (0.979 g, 8.57 mmol) was added and the mixture was stirred at 0° C. for 30 min and warmed up to room temperature for 2 h. Solvent was removed and the residue was chromatographed to afford 5-chloro-1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-N-(2-(pyrrolidin-1-yl)ethyl)-1,4-dihydrocinnoline-3-carboxamide (1.2 g, 1.932 mmol, 33.8% yield). LCMS: (M+H)+: 621.2

Aufarbeitung

stirringthe mixture was stirred at 0° C. for 30 min
temperaturewarmed up to room temperature for 2 h
customSolvent was removed
customthe residue was chromatographed

Quellen und Nachweise

ORD-Eintrag: ord-a604e812734c430f9815b2988f7e8052
Quelldatensatz: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09340556B2

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